TW201943715A - Bicyclic compound and use thereof for inhibiting histone methyltransferase - Google Patents

Abstract

The present invention relates to a compound represented by formula (I), a method for the preparation thereof, and a pharmaceutical composition containing the compound as an active ingredient for inhibiting histone methyltransferase such as SUV39H2.

Description

   Bicyclic compound and use thereof for inhibiting histone methyltransferase   

The present invention relates to a compound having an inhibitory activity against SUV39H21, a preparation method thereof, and a pharmaceutical composition containing the compound as an active ingredient. The present invention relates to a method for treating or preventing diseases related to histone methyltransferase, such as SUV39H2, which is overexpressed.

Nucleosome, the basic unit of DNA packaging in eukaryote, which consists of 147 base-pairs of DNA wrapped around the core of histone protein in sequence, and is the basic structure of chromatin. Unit [non-patent document 1]. All four core histones (H3, H4, H2A, and H2B) have unstructured N-terminal tails, and the N-terminus of these histones is particularly subject to various post-translational modifications: acetylation, alpha Methylation, phosphorylation, ubiquitination, SUMOylation, and ADP-ribosylation [Non-Patent Document 2]. These histone modifications cause dynamic changes in the structure of chromatin, thereby affecting transcriptional regulation, DNA replication, DNA repair, and alternative splicing [Non-Patent Documents 3 and 4]. Among epigenetic markers on these histones, the methylation process is particularly important for transcriptional regulation [Non-Patent Document 5]. Five lysine residues (H3K4, H3K9, H3K27, H3K36, and H4K20) are located at the N-terminal tail and are mono-, di-, or trimethylated Representative lysine. The methylation of H3K9, H3K27, and H4K20 mainly inhibits transcription, and the methylation markers on H3K4 and H3K36 are related to induction of active transcription [Non-Patent Document 6]. For example, methylation of histone H3 in lysine 9 (H3K9) is one of the most abundant and stable histone modifications, and is involved in gene suppression and heterochromatin formation. H3K9 can be mono-, di-, or trimethylated on H3K9, while the silent euchromatin region is rich in mono- and dimethylated H3K9 [Non-Patent Document 17]. In mammals, the heterochromatin region is highly trimethylated on H3K9, while the silent true chromatin region is rich in mono- and dimethylated H3K9 [Non-Patent Document 17]. H3K9 methylation has been linked to de novo gene silencing and DNA methylation, and is inherited after mitosis in a manner coupled to DNA methylation.

Some histone methyltransferases and demethylases have been previously reported to be extremely relevant to human carcinogenesis [Non-Patent Documents 7, 8, 9, 10, and 11]. For example, SMYD3, PRMT1, PRMT6, SUV420H1, and SUV420H2 have been shown to stimulate cell proliferation through their enzyme activity [Non-Patent Documents 1, 8, 9, 12, 13, 14, and 18].

SUV39H2, also known as KMT1B [Non-Patent Document 15], is a SET-domain containing histone methyltransferase and is known to methylate H3K9 lysine residues. The human homologue of human SUV39H2, Suv39h2 has been isolated and characterized as the second murine Suv39h gene, and has shown a 59% identity with Suv39h1 [Non-Patent Document 16]. The expression of Suv39h2 is limited to adult testes, and immunolocalization of endogenous Suv39h2 protein shows that it is abundantly distributed in heterochromatin during the first meiotic prophase and early sperminogenesis. During the mid-pachytene period, Suv39h2 specifically accumulated in the chromatin of silenced sex chromosomes present in the XY body. In addition, the histone methyltransferase activity of Suv39h2 appears to play an important role in regulating high-order chromatin dynamics during male meiosis [non-patent document 16].

    Reference list         Patent documents    

1. WO2005 / 071102

    Non-patent documents    

1. Strahl BD et al. Nature 2000; 403: 41-45; 2. Kouzarides T et al. Cell 2007; 128: 693-705; 3. Huertas D et al. Epigenetics 2009; 4: 31-42; 4. Luco RF et al. Science 2010; 327: 996-1000; 5. Kouzarides T et al. Curr Opin Genet Dev 2002; 12: 198-209; 6. Peterson CL et al. Curr Biol 2004; 14: R546-551; 7. Cho HS et al. Cancer Res 2010; 8. Hamamoto R et al. Nat Cell Biol 2004; 6: 731-40; 9. Hamamoto R et al. Cancer Sci 2006; 97: 113-8; 10. Yoshimatsu M et al. Int J Cancer 2011; 128: 562-573; 11. Hayami S et al. Int J Cancer 2011; 128: 574-586; 12. Kunizaki M et al. Cancer Res 2007; 67: 10759-65; 13 Silva FP et al. Oncogene 2008; 27: 2686-92; 14. Tsuge M et al. Nat Genet 2005; 37: 1104-7; 15. Allis CD et al. Cell 2007; 131: 633-636; 16. O'Carroll D et al. Mol Cell Biol 2000; 20: 9423-9433; 17. Martin C et al. Nat Rev Mol Cell Biol 2005; 6: 838-49; and 18. Schneider R et al. Trends Biochem Sci 2002 ; 27: 396-402.

The present inventors have devoted to the development of effective inhibitors of histone methyltransferase, especially SUV39H2, and have found compounds that can selectively inhibit the activity of SUV39H2.

This specification contains the disclosure of the following inventions.

[1] A compound represented by formula (I) or a pharmaceutically acceptable salt thereof:

Wherein R ¹ and R ^{2 are} independently selected from the group consisting of halogen atom, hydroxy, C ₁ -C ₆ alkyl and C ₁ -C ₆ alkoxy; R ^{3 is} independently selected from halogen Atom, cyano, nitro, hydroxyl, carboxyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, (C ₁ -C ₆ alkoxy) carbonyl ( carbonyl), C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl and C ₁ -C ₆ alkylsulfonyl; n Is an integer selected from 0 to 3; R ⁴ is selected from the group consisting of a hydrogen atom and a halogen atom; R ^{5 is} independently selected from the group consisting of a halogen atom, a C ₁ -C ₆ alkyl group, and a C ₁ -C ₆ alkoxy group A group consisting of; m is an integer selected from 0 to 3; X and Y are independently selected from a direct bond, -CH ₂ -and -CH ₂ CH _2- ; R ^{6 is} selected from one or more C ₁ -C ₆ alkyl substituted with a substituent selected from Ra, C ₃ -C ₁₀ cycloalkyl optionally substituted with one or more substituents selected from Rb, optionally substituted with one or C ₆ -C ₁₀ aryl substituted with multiple substituents selected from Rb, 5 to 10 optionally substituted with one or more substituents selected from Rb Heteroaryl, 3 to 12-membered non-aromatic heterocyclyl optionally substituted with one or more substituents selected from Rb, (C ₁ -C ₆ alkoxy) carbonyl substituted with a substituent, (C ₁ -C ₆ alkyl) carbonyl substituted with one or more substituents selected from Ra, one or more substituted with Rc (C ₃ -C ₁₀ cycloalkyl) carbonyl substituted with one or more (C ₆ -C ₁₀ aromatic) carbonyl substituted with one or more substituents selected from Rd, one or more substituents selected from Rc Substituted (3- to 12-membered non-aromatic heterocyclic) carbonyl, (5- to 10-membered heteroaryl) carbonyl substituted with one or more substituents selected from Rc, aminocarbonyl, (C ₁ -C ₆ alkyl) aminocarbonyl and di (C ₁ -C ₆ alkyl) aminocarbonyl; R ^{7 is} selected from a hydrogen atom and optionally via one or more substituents selected from Ra A group consisting of a substituted C ₁ -C ₆ alkyl group; Q is selected from a C ₁ -C ₆ alkylene group; R ^{10 is} independently selected from a group consisting of a halogen atom and a C ₁ -C ₆ alkyl group Group; q is an integer selected from 0 to 4; Ra is independently selected from the group consisting of a halogen atom, a hydroxyl group, C ₁ -C ₆ alkoxy, cyano, (C ₁ -C ₆ alkoxy) carbonyl, carboxyl, (C ₁ -C ₆ alkoxy) carbonylamino, (C ₁ -C ₆ alkyl) (C ₁ -C ₆ alkyl) carbonylamino, amine, C ₁ -C ₆ alkylamino, bis (C ₁ -C ₆ alkyl) amino, aminocarbonyl (C ₁ -C ₆ alkyl) aminocarbonyl, di (C ₁ -C ₆ alkyl) aminocarbonyl, C ₁ -C ₆ alkylsulfonylamino, C ₃ -C ₁₀ ring Cycloalkylsulfonylamino, C ₃ -C ₁₀ cycloalkyl optionally substituted with one or more substituents selected from Rc, optionally with one or more substituents selected from Rc A substituted C ₃ -C ₁₀ cycloalkenyl, a C ₆ -C ₁₀ aromatic group optionally substituted with one or more substituents selected from Rd, and optionally one or more selected from Rc 5 to 10 membered heteroaromatic groups substituted with substituents and 4 to 12 membered non-aromatic heterocyclic groups optionally substituted with one or more substituents selected from Rc; Rb is independently selected from halogen An atom, a hydroxyl group, a C ₁ -C ₆ alkyl group optionally substituted with one or more substituents selected from Ra, C ₁ -C ₆ alkoxy optionally substituted with one or more substituents selected from Ra, cyano, (C ₁ -C ₆ alkoxy) carbonyl, carboxyl, -NR ²¹ R ²² , -CONR ²³ R ²⁴ , bis (C ₁ -C ₆ alkyl) phosphono, C ₃ -C ₁₀ cycloalkyl optionally substituted with one or more substituents selected from Rc, optionally One or more C ₆ -C ₁₀ aromatic groups substituted with a substituent selected from Rd, 5 to 10 membered heteroaryl groups optionally substituted with one or more substituents selected from Rc, and optionally one or A group consisting of 3 to 12 non-aromatic heterocyclic groups substituted with a substituent selected from Rc; Rc is independently selected from C ₁ substituted by nitro, hydroxyl, optionally substituted by one or more halogen atoms -C ₆ alkyl, C ₁ -C ₆ alkoxy optionally substituted with one or more halogen atoms, halogen atom, amine, cyano, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylsulfonyl, C ₃ -C ₁₀ cycloalkane Sulfosulfenyl, C ₇ -C ₁₄ aralkyl optionally substituted with one or more substituents selected from Re, optionally with one or A plurality of C ₆ -C ₁₀ aromatic groups substituted with a substituent selected from Re, a C ₃ -C ₁₀ cycloalkyl group optionally substituted with one or more substituents selected from Re, optionally one or more 3 to 12 membered non-aromatic heterocyclic groups substituted with a substituent selected from Re, 5 to 10 membered heteroaromatic groups optionally substituted with one or more substituents selected from Re and oxo A group consisting of; Rd is independently selected from C ₁ -C ₆ alkyl substituted by nitro, hydroxyl, optionally substituted by one or more halogen atoms, C ₁ optionally substituted by one or more halogen atoms -C ₆ alkoxy, halogen atom, amine, cyano, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkylcarbonyl, (C _1- C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylsulfonyl, C ₃ -C ₈ cycloalkylsulfonyl, C optionally substituted with one or more substituents selected from Re _7- C ₁₄ aralkyl, C ₆ -C ₁₀ aryl, optionally substituted with one or more substituents selected from Re, C ₃ , optionally substituted with one or more substituents selected from Re -C ₈ cycloalkyl, optionally substituted with one or more substituents of 3-12 non-aromatic heteroatom selected from Re, And 5 to 10 membered heteroaryl groups optionally substituted with one or more substituents selected from Re; Re is independently selected from the group consisting of nitro, hydroxyl, optionally via one or more halogens Atom-substituted C ₁ -C ₆ alkyl, halogen atom, amine, cyano, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkyl Carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylsulfonyl and C ₃ -C ₈ cycloalkylsulfonyl; R ^{21 is} selected from the group consisting of a hydrogen atom, C ₁ -C ₆ alkyl substituted with one or more substituents selected from Ra, C ₆ -C ₁₀ aromatic substituted with one or more substituents selected from Rd, optionally 4- to 12-membered heterocyclic groups substituted with one or more substituents selected from Rc, 5- to 10-membered heteroaromatic groups optionally substituted with one or more substituents selected from Rc, optionally Or (C ₁ -C ₆ alkoxy) carbonyl substituted with a substituent selected from Ra, (C ₁ -C ₆ alkyl) carbonyl optionally substituted with one or more substituents selected from Ra, (C ₃ -C ₁₀ cycloalkyl) carbonyl, (C ₆ -optionally substituted with one or more substituents selected from Rd C ₁₀ aryl) carbonyl, optionally substituted with one or more substituents selected from Rc (3- to 12-membered non-aromatic heterocyclic group) carbonyl, optionally substituted with one or more substituents selected from Rc (C ₁ -C ₆ alkyl) aminocarbonyl-substituted (5-10 heteroaromatic group) carbonyl, aminocarbonyl, optionally substituted by one or more substituents selected from Ra selectively two (C ₁ -C ₆ alkyl) aminocarbonyl group Ra is selected from substituted by one or more selectively by one or more halogen atoms substituted C ₁ -C ₆ alkylsulfonyl group, C ₇ -C ₁₄ aralkylsulfonyl, C ₃ -C ₁₀ cycloalkylsulfonyl, aminesulfonyl, C ₁ -C ₆ alkylaminosulfonyl, di (C ₁ -C ₆ A group consisting of alkyl) aminosulfonyl and di (C ₁ -C ₆ alkyl) phosphinofluorenyl; R ^{22 is} selected from the group consisting of a hydrogen atom and optionally substituted with one or more substituents selected from Ra R ₁ -C ₆ alkyl group; R ^{23 is} selected from C ₁ -C ₆ alkyl group optionally substituted by hydrogen atom, optionally substituted by one or more substituents selected from Ra, Ra is selected from one or more substituents [(C ₁ -C ₆ alkyl) amino] C ₁ -C ₆ alkyl, optionally substituted with one or Ra is selected from substituted group substituted [di- (C ₁ -C ₆ alkyl) amino] C ₁ -C ₆ alkyl, optionally substituted with one or more substituents selected from Rc, substituted C ₃ - C ₁₀ cycloalkyl, C ₆ -C ₁₀ aromatic optionally substituted with one or more substituents selected from Rd, 5 to 10 members optionally substituted with one or more substituents selected from Rd A heteroaromatic group and a 3- to 12-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Rc; and R ^{24 is} selected from a hydrogen atom and optionally via one or A plurality of C ₁ -C ₆ alkyl groups substituted with a substituent selected from Ra.

[2] The compound or a pharmaceutically acceptable salt thereof according to [1], wherein R ⁷ is a hydrogen atom.

[3] The compound or a pharmaceutically acceptable salt thereof according to [1] or [2], wherein R ^{6 is} selected from a pyrimidyl group, optionally a halogen atom, or a C ₁ -C ₆ alkoxy group Group-substituted pyridyl, piperidyl optionally substituted with a C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group, optionally C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group substituted pyrrolidyl, optionally with a di (C ₁ -C ₆ alkyl) amino group Or C ₁ -C ₆ alkyl group substituted C ₃ -C ₇ cycloalkyl, tetrahydrofuryl, tetrahydropyranyl, benzene optionally substituted with a substituent selected from Rb A group consisting of a group, a group -CH ₂ -Ra, a group -CH ₂ CH ₂ -Ra, and a group -CH ₂ CH ₂ CH ₂ -Ra.

[4] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [3], wherein Ra is independently selected from the group consisting of hydroxyl, C ₁ -C ₆ alkoxy, optionally (C ₁ -C ₆ alkyl) amino groups substituted C ₃ -C ₇ cycloalkyl, phenyl optionally substituted with one or more substituents selected from Rd, optionally C _1- C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group substituted pyrrolidinyl, optionally via C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) Carbonyl group-substituted piperidinyl, pyridyl optionally substituted with a halogen atom or a C ₁ -C ₆ alkoxy group, thiazolyl, thienyl, optionally di (C ₁ -C ₆ alkyl) amino group substituted pyrimidinyl and C ₃ -C ₇ cycloalkenyl.

[5] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [4], wherein Rb and Rd are independently selected from a halogen atom, a methyl group, and a cyanodimethylamino group ( cyano dimethylamino), methoxy, nitro, hydroxy, and trifluoromethyl.

[6] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [5], wherein the aforementioned compound is represented by formula (Ib):

Q is selected from -CH _2- , -CH (CH ₃ )-, -CH (CH ₂ CH ₃ )-, -CH ₂ CH _2- , -CH (CH ₃ ) CH _2- , and -CH ₂ CH (CH ₃ )-A group consisting of; -R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, Y, m and n from any one of [1] to [5] As defined.

[7] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [6], wherein X and Y are-(CH ₂ )-, or X is a direct bond And Y is-(CH ₂ )-.

[8] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [7], wherein the aforementioned compound is represented by formula (Ic):

Wherein R ¹ and R ^{2 are} independently selected from the group consisting of C ₁ -C ₆ alkoxy groups, p is an integer selected from 0 and 1; R ³ is selected from the group consisting of halogen atoms, and R ⁶ And R ⁷ are defined by any one of [1] to [6].

[9] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [7], wherein R ¹ and R ² are a methoxy group, and R ³ is a chlorine atom.

[10] The compound or a pharmaceutically acceptable salt thereof according to [1], which is selected from the group consisting of 1- (1- (2- (5-chloro-2,4-dimethylamine) Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopropylmethyl) methylamine (1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopropylmethyl) methanamine); 1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopentylmethyl) methylamine (1- ( 1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopentylmethyl) methanamine); 3-((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) Tert-Butyl 3- (methyl) pyrrolidine-1-carboxylate (((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin-7 -yl) piperidin-4-yl) methyl) amino) methyl) pyrrolidine-1-carboxylate); 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazole (1,2-a) pyridine-7-yl) piperidin-4-yl) methyl) (methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl tert-Butyl 3- ((((1- (2- (5-chlor o-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) (methyl) amino) methyl) pyrrolidine-1-carboxylate); 1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyrrolidin-3-yl Methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyrrolidin -3-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- 4-yl) -N- (cyclohexylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin -4-yl) -N- (cyclohexylmethyl) methanamine); 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4-((((1- (2- (5- chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidine-1-carboxylate); 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (piperidin-4-ylmethyl) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) im idazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (piperidin-4-ylmethyl) methanamine); N-benzyl-1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methylamine (N-Benzyl-1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methanamine); 1- (1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-methylbenzyl) methylamine (1- (1- (2 -(5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-methylbenzyl) methanamine); 1- (1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methylbenzyl) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl)- N- (2-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) -N- (2-fluorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- (Yl) piperidin-4-yl) -N- (3-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin -7-yl) piperidin-4-yl) -N- (3-fluorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) piperidin-4-yl) -N- (4-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethylamine) Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxybenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxybenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-chlorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-chlorobenzyl) methanamine) ; 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) (Methyl) amino) methyl) -N, N-dimethylaniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin -7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylaniline); 3-((((((1- (2- (5-chloro-2,4-dimethoxybenzene Yl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile (3-(((((1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile); 4-(((((1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile ( 4-((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile) ; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-nitrobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-nitrobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Piperidin-4-yl) -N- (3- (trifluoromethyl) benzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-4-yl) -N- (3- (trifluoromethyl) benzyl) methanamine); 1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyridin-3-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyridin-3-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl)- N- (pyridin-4-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4 -yl) -N- (pyridin-4-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine -7-yl) piperidin-4-yl) -N-((3-fluoropyridin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl ) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((3-fluoropyridin-4-yl) methyl) methanamine); 1- (1- (2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((2-methoxypyridin-4-yl ) Methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( (2-methoxypyridin-4-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) (1- (1- (2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) methanamine); 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N, N-bis (pyridin-2-ylmethyl) Methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N, N-bis (pyridin-2-ylmethyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) Piperidin-4-yl) methyl) cyclobutylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin- 4-yl) methyl) cyclobutanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piper Pyridin-4-yl) methyl) cyclopentylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl ) piperidin-4-yl) methyl) cyclopentanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- (Yl) piperidin-4-yl) methyl) tetrahydrofuran-3-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7- yl) piperidin-4-yl) methyl) tetrahydrofuran-3-amine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) piperidin-4-yl) methyl) cyclohexylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin -7-yl) piperidin-4-yl) methyl) cyclohexanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) piperidin-4-yl) methyl) tetrahydro-2H-pyran-4-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) tetrahydro-2H-pyran-4-amine); N-((1- (2- (5-chloro-2,4-di (Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cycloheptylamine (N-((1- (2- (5-Chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cycloheptanamine); N-((1- (2- (5-chloro-2,4-dimethyl) Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -1-methyl Piperidine-4-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -1-methylpiperidin-4-amine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Piperidin-4-yl) methyl) -1-isopropylpiperidine-4-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] pyridin-7-yl) piperidin-4-yl) methyl) -1-isopropylpiperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazole Benzo [1,2-a] pyridine-7-yl) piperidin-4-yl) -N-((1-methylpiperidin-4-yl) methyl) methylamine (1- (1- (2 -(5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-methylpiperidin-4-yl) methyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) 2- (1-methylpiperidin-4-yl) ethylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7- yl) piperidin-4-yl) methyl) -2- (1-methylpiperidin-4-yl) ethanamine); N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl)- N ⁴ , N ⁴ -Dimethylcyclohexane-1,4-diamine (N ¹ -((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -N ⁴ , N ⁴ -dimethyl cyclohexane-1,4-diamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidin-3-yl) -N- (cyclopropylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7 -yl) pyrrolidin-3-yl) -N- (cyclopropylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) pyrrolidin-3-yl) -N- (cyclopentylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cyclopentylmethyl) methanamine); 3-(((((1- (2- (5-chloro-2,4-dimethoxybenzene (Yl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-Butyl 3- ( (((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylate ); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(Pyrrolidin-3-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3 -yl) -N- (pyrrolidin-3-ylmethyl) metha namine); 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- Tert-Butyl 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (piperidin-4-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (piperidin-4-ylmethyl) methanamine); N-benzyl-1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methylamine (N- Benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methanamine); 1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-fluorobenzyl) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-fluorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridin-7-yl) pyrrolidin-3-yl) -N- (3-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridin-7-yl) pyrrolidin-3-yl) -N- (3-fluorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl)) Imidazolo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-fluorobenzyl) methanamine); 4-((((((1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N-dimethyl Aniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl ) -N, N-dimethylaniline); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Pyrrolidin-3-yl) methyl) amino) methyl) phenol (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin -7-yl) pyrrolidin-3-yl) methyl) amino) methyl) phenol); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a) pyridine-7-yl) pyrrolidin-3-yl) -N- (2-nitrobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4 -dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-nitrobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (3- (trifluoromethyl) benzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (3- (trifluoromethyl) benzyl) methanamine) ; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4- (trifluoromethyl) benzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin- 3-yl) -N- (4- (trifluoromethyl) benzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) pyrrolidin-3-yl) -N- (4-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxybenzene) Yl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-chlorobenzyl) methylamine (1- (1- (2- (5-Chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-chlo robenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) -N- (4-chlorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3 -yl) -N- (4-chlorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) -N- (pyridin-3-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyridin-3-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyridin-4-ylmethyl) methylamine (1- (1- (2- (5-Chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyridin-4-ylmethyl) methanamine); 1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((3-fluoropyridin-4-yl) Methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-(( 3-fluoropyridin-4-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imide Benzo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((2-fluoropyridin-4-yl) methyl) methylamine (1- (1- (2- ( 5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((2-fluoropyridin-4-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N, N-di (Pyridin-2-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) -N, N-bis (pyridin-2-ylmethyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) pyrrolidin-3-yl) methyl) -2-methoxyethylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-methoxyethanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazole Benzo [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) cyclobutylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cyclobutanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) -1-methylpiperidine-4-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-methylpiperidin-4-amine); 1- (1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methyl Piperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3 -yl) -N-((1-methylpiperidin-4-yl) methyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) aniline (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] pyridin-7-yl) pyrrolidin-3-yl) methyl) aniline); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) pyrrolidin-3-yl) methyl) -2-phenylethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-phenylethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethyl) (Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thien-2-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiophen-2-ylmet hyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- (Methyl) methyl) -2- (1-methylpyridin-4-yl) ethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2- (1-methylpiperidin-4-yl) ethan-1-amine); N-benzyl-1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methylamine (N-Benzyl-1- ( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methanamine); 4- (2-(((1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) ethyl) piper Tert-Butyl 4- (2-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl ) piperidin-4-yl) methyl) amino) ethyl) piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a) pyridine-7-yl) azetidin-3-yl) -N- (4-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl ) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (4-fluorobenzyl) methanamine); 3-(((((1- (2- (5- (5- -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) azetidin-3-yl) methyl) amino) methyl) pyrrolidine-1 -Tert-Butyl carboxylic acid (tert-Butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3- yl) methyl) amino) methyl) pyrrolidine-1-carboxylate); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2- a) Pyridine-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4-((((1- ( 2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) -methyl) piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (Cyclopentylmethyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (cyclopentylmethyl) -methanamine); 4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) pyrrolidin-3-yl) methyl) amino) ethyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (2-(((1- (2- (5 (5 -chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl ) pyrrolidin-3-yl) methyl) amino) ethyl) -piperidine-1-carboxylate); 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) piperidin-3-yl) methyl) amino) methyl) -pyrrolidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) -pyrrolidine-1-carboxylate) ; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (1-Isopropylpiperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7- yl) pyrrolidin-3-yl) -N-((1-isopropylpiperidin-4-yl) methyl) methanamine); 2-(((((1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline (2-(((( 1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( 2,4-dimethoxybenzyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimet hoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2,4-dimethoxybenzyl) -methanamine); 2-(((((1- (2- (5- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N-di Methylaniline (2-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylaniline); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) nitrogen Heterocyclobutane-3-yl) -N- (cyclohexylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin- 7-yl) azetidin-3-yl) -N- (cyclohexylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) piperidin-4-yl) -N- (4-methoxy-2-nitrobenzyl) methylamine (1- (1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxy-2-nitrobenzyl) methanamine); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline); 5-(((((1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -2-methoxyphenol (5- ((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -2-methoxyphenol ); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) -N -(Cyclohexylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl)- N- (cyclohexylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine- 3-yl) -N- (4-fluoro-3-methylbenzyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-fluoro-3-methylbenzyl) -methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxybenzene (Yl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-methoxy-3-methylbenzyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-meth oxy-3-methylbenzyl) -methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrole Alk-3-yl) -N- (2-fluoro-4-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-fluoro-4-methylbenzyl) methanamine); N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl)- N4, N4-dimethylcyclohexane-1,4-diamine (N ¹ -((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -N4, N4-dimethylcyclohexane-1, 4-diamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) -N- (3-fluoro-4-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7- yl) pyrrolidin-3-yl) -N- (3-fluoro-4-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) pyrrolidin-3-yl) -N- (2,4-difluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2,4-difluorobenzyl) methanamine; N-((1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-isopropylpiperidine-4-amine (N -((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-isopropylpiperidin-4-amine) ; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- ((1-ethylpiperidin-4-yl) methyl) propan-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) propan-1-amine); 1- (tert-butyl)- N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl ) Piperidine-4-amine (1- (tert-Butyl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl ) piperidin-4-yl) methyl) piperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine -7-yl) piperidin-4-yl) -N-((1-ethylpiperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4 -dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-ethylpiperidin-4-yl) methyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (1-ethylpiperidine Pyridin-pyridin-4-yl) ethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin- 4-yl) methyl) -2- (1-ethylpiperidin-4-yl) ethan-1-amine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl)) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cycloheptylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cycloheptanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) pyrrolidin-3-yl) methyl) -1-ethylpiperidine-4-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-ethylpiperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethyl) Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2,4-dimethoxybenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2,4-dimethoxybenzyl) methanamine); 1- ( Tert-butyl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- (Methyl) methyl) piperidine-4-amine (1- (tert-Butyl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin- 7-yl) pyrrolidin-3-yl) methyl) piperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) me thyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4- (Methyl) methyl) -2-cyclopentylethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl ) piperidin-4-yl) methyl) -2-cyclopentylethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) azetidin-3-yl) -N- (2-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl ) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (2-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-di (Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxy-3-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxy-3-methylbenzyl) methanamine ); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine-3- (Methyl) -3,3-dimethylbut-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7 -yl) azetidin-3-yl) methyl) -3,3-dimethylbutan-1-amine); 2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl)) Zolo [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) -5-methoxyphenol (2-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -5-methoxyphenol); 5-(((((1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl ) -2-methoxyphenol (5-((((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) methyl) amino) methyl) -2-methoxyphenol); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- ) Azetidin-3-yl) -N- (4-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridin-7-yl) azetidin-3-yl) -N- (4-methylbenzyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2- (1-propylpiperidin-4-yl) ethyl-1-amine (N- ( (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2- (1-propylpiperidin-4-yl ) ethan-1-amine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine -7-yl) pyrrolidin-3-yl) methyl) -2- (1-ethylpiperidin-4-yl) ethyl-1-amine (N-((1- (2- (5-Chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2- (1-ethylpiperidin-4-yl) ethan-1-amine); 1- ( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1- Methylpyrrolidin-3-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin- 4-yl) -N-((1-methylpyrrolidin-3-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) piperidin-4-yl) -N-((1-ethylpiperidin-3-yl) methyl) methylamine (1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-ethylpiperidin-3-yl) methyl) methanamine); 3- ( (((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amine Tert-Butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a) pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-di (Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cycloheptylmethyl) -methylamine (1- (1- (2- ( 5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cycloheptylmethyl) -methanamine); 1- (4-(((((1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl ) Piperidin-1-yl) -2,2-dimethylpropan-1-one (1- (4-((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidin-1-yl) -2,2-dimethylpropan-1-one); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (1-propylpiperidine Pyridin-4-yl) ethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4- yl) methyl) -2- (1-propylpiperidin-4-yl) ethan-1-amine); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl)) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N, 3-trimethylaniline (4-((((1 -(2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N, 3-tri methylaniline); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl)- N- (cyclohexylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cyclohexylmethyl) methanamine); 4-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidin-3-yl) methyl) amino) azacycloheptane-1-carboxylic acid tert-butyl ester (tert-Butyl 4-(((1- (2- (5-chloro-2,4-dimethoxyphenyl ) imidazo- [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) azepane-1-carboxylate); 4-((((((1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -3-methoxy-N, N-dimethylaniline (4-((((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl ) amino) methyl) -3-methoxy-N, N-dimethylaniline); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) azetidin-3-yl) -N- (3-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (3-methylbenzyl ) methanamine); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3 -Yl) methyl) amino) methyl) -N, N, 2-trimethylaniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N, 2-trimethylaniline); 4-(((((1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N, 2-trimethyl Aniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N, 2-trimethylaniline); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Yl) piperidin-4-yl) methyl) amino) methyl) -2-methoxy-N, N-dimethylaniline (4-(((((1- (2- (5-Chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -2-methoxy-N, N-dimethylaniline); 1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-isobutyl Piperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pipe ridin-4-yl) -N-((1-isobutylpiperidin-4-yl) methyl) methanamine); 2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 2 -((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine- 1-carboxylate); 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azacyclo Butane-3-yl) methyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-((((1- (2- (5-chloro-2,4 -dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -piperidine-1-carboxylate); 1- (1- (tert-butyl) pyrrolidine -3-yl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3 -Yl) methyl) methylamine (1- (1- (tert-Butyl) pyrrolidin-3-yl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) methanamine); 1- (1- (methyl) pyrrolidin-3-yl) -N-((1- (2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) pyrrole -3-yl) methyl) methylamine (1- (1- (methyl) pyrrolidin-3-yl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a) pyridine-7-yl) pyrrolidin-3-yl) -N-((1-methylpyrrolidin-3-yl) methyl) methylamine (1- (1- (2- (5- ( Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpyrrolidin-3-yl) methyl) methanamine); N-(( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -4-methyl Cyclohexan-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -4-methylcyclohexan-1-amine); 6-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylpyridin-3-amine (6-((((1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylpyridin-3-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N -(2-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (2-fluorobenzyl) methanamine); 1- (4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) piperidin-4-yl) methyl) amino) ethyl) piperidin-1-yl) -2,2-dimethylpropan-1-one (1- (4- (2-(((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) ethyl) piperidin- 1-yl) -2,2-dimethylpropan-1-one); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) pyrrolidin-3-yl) methyl) -2-cycloheptylethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-cycloheptylethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpiperidin-3-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpiperidin-3-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) -N-((1-ethylpiperidin-3-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-3-yl) methyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethylamine Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -4-ethylcyclohex-1-amine (N-((1- (2 -(5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -4-ethylcyclohexan-1-amine); 1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (3-fluoro Benzyl) methylamine 1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (3- fluorobenzyl) methanamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluoro-3-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl ) piperidin-4-yl) -N- (4-fluoro-3-methylbenzyl) methanamine); 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazole (1,2-a) pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl tert-Butyl 3- ((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) -piperidine- 1-carboxylate); 2-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azacyclo Butane-3-yl) methyl) amino) methyl) -N, N-dimethylaniline (2-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline); 1- (1- (2- (5-chloro-2,4-di (Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluoro-3-methylbenzyl) methylamine (1- (1 -(2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluoro-3-methylbenzyl) methanamine); 3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1, 2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1- (cyclobutylmethyl ) -Piperidin-4-yl) methyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1- (cyclobutylmethyl) -piperidin-4-yl) methyl) -methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2,3-dimethylbenzyl) -methylamine (1- (1- (2 -(5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2,3-dimethylbenzyl) -methanamine); N- (1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) -1 -Ethylpiperidine-4-amine (N- (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3- yl) ethyl) -1-ethylpiperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) ethan-1-amine); 1- (1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-cyclohexyl B ) Ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( 2-cyclohexylethyl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Piperidin-4-yl) -N- (2-fluoro-3-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-4-yl) -N- (2-fluoro-3-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-methoxy-5-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-methoxy-5-methylbenzyl) methanamine); 1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2 -Cyclopentylethyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3- yl) -N- (2-cyclopentylethyl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) pyrrolidin-3-yl) -N- (cycloheptylmethyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imida zo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cycloheptylmethyl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-fluoro-5-methylbenzyl) methylamine (1- ( 1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-fluoro-5-methylbenzyl) methanamine) ; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl ) -2- (cyclohex-1-en-1-yl) ethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (cyclohex-1-en-1-yl) ethan-1-amine); N-((1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-cyclopentylethyl-1-amine (N- ( (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-cyclopehtylethan-1-amine); 4 -(3-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) (Methyl) amino) propyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (3-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyri din-7-yl) pyrrolidin-3-yl) methyl) amino) propyl) piperidine-1-carboxylate); 4- (2-((1- (1- (2- (5-chloro-2,4-di Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester (tert- Butyl 4- (2-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino ) ethyl) piperidine-1-carboxylate); N ¹ -(1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl ) -N ⁴ , N ⁴ -Dimethylcyclohexane-1,4-diamine (N ¹ -(1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) -N ⁴ , N ⁴ -dimethylcyclohexane-1,4-diamine); 4-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) piperidin-4-yl) ethyl) amino) methyl) -benzonitrile (4-(((2- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -benzonitrile); 4-(((2- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4-((((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylate); N-benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) piperidin-4-yl) ethyl-1-amine (N-Benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethan-1-amine); 3-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) ethyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) m ethyl) -piperidine-1-carboxylate); 4- (3-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) pyrrolidin-3-yl) ethyl) amino) propyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (3-((1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) propyl) -piperidine-1-carboxylate); 1- ( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1- Methylpiperidin-4-yl) methyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl ) pyrrolidin-3-yl) -N-((1-methylpiperidin-4-yl) methyl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2- (1-propylpiperidin-4-yl) ethyl) ethyl-1- Amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2- (1- propylpiperidin-4-yl) ethyl) ethan-1-amine); 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a) pyridine-7-yl) piperidin-4-yl) ethyl) amino) methyl) -pyrrolidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((2- (1- (2-( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -pyrrolidine-1-carboxylate); 4- (3- ( (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl ) Amino) -propyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (3-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) -propyl) piperidine-1-carboxylate); 2-(((((1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -4-methylphenol (2- ((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -4-methylphenol ); 4-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) ethyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl ) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylate); 3-((((((1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- 4-yl) ethyl) amino) methyl) -pyrrolidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((1- (1- (2- (5-chloro-2,4- dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -pyrrolidine-1-carboxylate); 2- (1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) ethyl-1-amine (2- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- ( (1-isopropylpyrrolidin-3-yl) methyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin -7-yl) pyrrolidin-3-yl) -N-((1-isopropylpyrrolidin-3-yl) methyl) ethan-1-amine); 1- (tert-butyl) -N- (1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) piperidine-4-amine ( 1- (tert-Butyl) -N- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) piperidin-4-amine); 3-(((((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [ 1,2-a] pyridine-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylate ); N-benzyl-2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) ethyl-1-amine (N-Benzyl-2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4- yl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) -N- (cyclopentylmethyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin- 7-yl) piperidin-4-yl) -N- (cyclopentylmethyl) ethan-1-amine); 3-(((((1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-Butyl 3- (((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) pyrrolidine -1-carboxylate); N- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridin-7-yl) piperidin-4-yl) ethyl) cyclohexylamine (N- (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) cyclohexanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) piperidin-4-yl) -N-phenethylethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-4-yl) -N-phenethylethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) piperidin-4-yl) -N- (2-cyclopentylethyl) ethyl-1-amine (1- (1- (2- (5-Chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-cyclopentylethyl) ethan-1-amine); 3-(((((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) (Methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a ] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) ethyl-1-amine (1- (1- (2- (5-Chloro -2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) ethan-1-amine); and 1- (1- (2- (5- ( Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl ) Methyl) propan-2-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl)- N-((1-ethylpiperidin-4-yl) methyl) propan-2-amine); and the aforementioned pharmaceutically acceptable salts.

[11] A pharmaceutical composition comprising the compound according to any one of [1] to [10] or a pharmaceutically acceptable salt thereof as an active ingredient.

[12] Use of the pharmaceutical composition according to [11] for treating or preventing cancer.

[13] A pharmaceutical composition according to [12], wherein the cancer is selected from the group consisting of lung cancer, cervical cancer, bladder cancer, esophageal cancer, and osteosarcoma (osteosarcoma), prostate cancer (prostate cancer) and soft tissue tumor (soft tissue tumor).

[14] A method for treating or preventing a disease related to SUV39H2 overexpression, comprising administering to a subject in need thereof an effective amount of the compound according to any one of [1] to [10] or a medicament thereof Acceptable salt.

[15] A method according to [14], wherein the aforementioned disease is cancer.

[16] Use of the compound according to any one of [1] to [10] or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for treating or preventing a disease related to SUV39H2 overexpression.

This specification also includes the disclosure of the following inventions.

[1] A compound represented by formula (I) or a pharmaceutically acceptable salt thereof:

Wherein R ¹ and R ^{2 are} independently selected from the group consisting of halogen atom, hydroxy, C ₁ -C ₆ alkyl and C ₁ -C ₆ alkoxy; R ^{3 is} independently selected from halogen Atom, cyano, nitro, hydroxyl, carboxyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, (C ₁ -C ₆ alkoxy) carbonyl ( carbonyl), C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl and C ₁ -C ₆ alkylsulfonyl; n Is an integer selected from 0 to 3; R ⁴ is selected from the group consisting of a hydrogen atom and a halogen atom; R ^{5 is} independently selected from a hydrogen atom, a halogen atom, a C ₁ -C ₆ alkyl group, and a C ₁ -C ₆ alkane A group of oxy groups; m is an integer selected from 0 to 3; p is an integer selected from 0 and 1; R ^{6 is} selected from C ₁ -C ₆ substituted with one or more substituents selected from Ra Alkyl, C ₃ -C ₁₀ cycloalkyl optionally substituted with one or more substituents selected from Rb, C ₆ -optionally substituted with one or more substituents selected from Rb C ₁₀ aryl, 5 to 10-membered heteroaryl optionally substituted with one or more substituents selected from Rb, 3 to 12-membered non-aromatic heterocyclyl substituted with one or more substituents selected from Rb, (C _1- C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkyl) carbonyl substituted with one or more substituents selected from Ra, (C ₃ -C ₍₁₀ cycloalkyl) carbonyl, (C ₆ -C ₁₀ aromatic) carbonyl substituted with one or more substituents selected from Rd, (3 to 12 non-substituted Aromatic heterocyclyl) carbonyl, (5- to 10-membered heteroaromatic) carbonyl substituted with one or more substituents selected from Rc, aminocarbonyl, (C ₁ -C ₆ alkyl) amino A group consisting of a carbonyl group and a di (C ₁ -C ₆ alkyl) amino carbonyl group; R ^{7 is} selected from a C ₁ -C ₆ alkane substituted by a hydrogen atom and optionally substituted by one or more substituents selected from Ra group consisting of the group; or Ra is independently selected from the group consisting of a halogen atom, a hydroxyl group, C ₁ -C ₆ alkyl, cyano, (C ₁ -C ₆ alkoxy) carbonyl group, a carboxyl group, (C ₁ -C ₆ alkyl (Oxy) carbonylamino, (C ₁ -C ₆ alkyl) carbonylamino, amine , C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, aminocarbonyl, (C ₁ -C ₆ alkyl) aminocarbonyl, di (C _1- C ₆ alkyl) aminocarbonyl, C ₁ -C ₆ alkylsulfonylamino, C ₃ -C ₁₀ cycloalkylsulfonylamino, optionally C ₃ -C ₁₀ cycloalkyl substituted with a plurality of substituents selected from Rc, C ₆ -C ₁₀ aromatic substituted with one or more substituents selected from Rd, optionally with one or more A group of 5 to 10-membered heteroaromatic groups substituted with a substituent selected from Rc and 4 to 12-membered non-aromatic heterocyclic groups optionally substituted with one or more substituents selected from Rc; Rb Independently selected from C ₁ -C ₆ alkyl optionally substituted with a halogen atom, a hydroxyl group, optionally substituted with one or more substituents selected from Ra, C substituted optionally with one or more substituents selected from Ra _1- C ₆ alkoxy, cyano, (C ₁ -C ₆ alkoxy) carbonyl, carboxyl, -NR ²¹ R ²² , -CONR ²³ R ²⁴ , bis (C ₁ -C ₆ alkyl) phosphinofluorenyl (phosphono), a C ₃ -C ₁₀ cycloalkyl group optionally substituted with one or more substituents selected from Rc 5-10 heteroaromatic group selection and selectively with one or more substituents selected from Rd is C ₆ -C ₁₀ aryl, optionally substituted with one or more substituents selected from the group Rc, A group consisting of 3 to 12 non-aromatic heterocyclic groups substituted with one or more substituents selected from Rc; Rc is independently selected from nitro, hydroxyl, optionally with one or more halogens Atom-substituted C ₁ -C ₆ alkyl, halogen atom, amine, cyano, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, (C ₁ -C ₆ alkyl Carbonyl), (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylsulfonyl, C ₃ -C ₁₀ cycloalkylsulfonyl, optionally via one or more selected from Re C ₇ -C ₁₄ aralkyl substituted with a substituent, optionally C ₆ -C ₁₀ aryl substituted with one or more substituents selected from Re, optionally with one or more selected C ₃ -C ₁₀ cycloalkyl substituted with substituents of Re, 3 to 12-membered non-aromatic heterocyclic groups optionally substituted with one or more substituents selected from Re, optionally with one or more Selected from the group consisting of 5 to 10-membered heteroaryl groups and oxo groups substituted with Re substituents Rd is independently selected from the group consisting of nitro, hydroxy, optionally substituted with one or more halogen atoms substituted C ₁ -C ₆ alkyl, halogen, amino, cyano, C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkylcarbonyl, (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylsulfonyl, C ₃ -C ₈ ring Alkylsulfonyl, C ₇ -C ₁₄ aralkyl optionally substituted with one or more substituents selected from Re, C ₆ -optionally substituted with one or more substituents selected from Re C ₁₀ aryl, C ₃ -C ₈ cycloalkyl optionally substituted with one or more substituents selected from Re, 3 to 12 members optionally substituted with one or more substituents selected from Re Non-aromatic heterocyclic groups and 5- to 10-membered heteroaromatic groups optionally substituted with one or more substituents selected from Re; Re is independently selected from the group consisting of nitro, hydroxyl, and optionally C ₁ -C ₆ alkyl substituted with one or more halogen atoms, halogen atom, amine, cyano, C ₁ -C ₆ alkylamino, bis (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkylcarbonyl, (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylsulfonyl group and a C ₃ -C ₈ cycloalkyl alkylsulfonyl group consisting of Group; R ²¹ selected from the group consisting of a hydrogen atom, optionally substituted with one or more substituents selected from Ra is a C ₁ -C ₆ alkyl, optionally substituted by one or more substituents selected from the group of Rd C ₆ -C ₁₀ aromatic groups, 4- to 12-membered heterocyclic groups optionally substituted with one or more substituents selected from Rc, 5 to 12 optionally substituted with one or more substituents selected from Rc 10-membered heteroaryl, (C ₁ -C ₆ alkoxy) carbonyl optionally substituted with one or more substituents selected from Ra, optionally substituted with one or more substituents selected from Ra (C ₁ -C ₆ alkyl) carbonyl, (C ₃ -C ₁₀ cycloalkyl) carbonyl, (C ₆ -C ₁₀ aromatic) carbonyl optionally substituted with one or more substituents selected from Rd, (3 to 12-membered non-aromatic heterocyclic group) carbonyl optionally substituted with one or more substituents selected from Rc, (5 to 10 optionally substituted with one or more substituents selected from Rc Member heteroaromatic) carbonyl, aminocarbonyl, (C ₁ -C ₆ alkyl) aminocarbonyl optionally substituted with one or more substituents selected from Ra, optionally via one or more selected from two (C ₁ -C ₆ alkyl) aminocarbonyl group of substituents Ra, Optional substituted with one or more halogen atoms substituted C ₁ -C ₆ alkylsulfonyl group, C ₇ -C ₁₄ aralkyl alkylsulfonyl group, C ₃ -C ₁₀ cycloalkyl alkylsulfonyl group, a sulfo group Group consisting of fluorenyl, C ₁ -C ₆ alkylaminosulfonyl, bis (C ₁ -C ₆ alkyl) aminosulfonyl and bis (C ₁ -C ₆ alkyl) phosphinofluorenyl ; R ^{22 is} selected from the group consisting of a hydrogen atom and a C ₁ -C ₆ alkyl group optionally substituted with one or more substituents selected from Ra; R ^{23 is} selected from a hydrogen atom, optionally through one or C ₁ -C ₆ alkyl substituted with multiple substituents selected from Ra, [(C ₁ -C ₆ alkyl) amino] C ₁ -optionally substituted with one or more substituents selected from Ra C ₆ alkyl, [di (C ₁ -C ₆ alkyl) amino] optionally substituted with one or more substituents selected from Ra] C ₁ -C ₆ alkyl, optionally via one or more C ₃ -C ₁₀ cycloalkyl substituted with a substituent selected from Rc, C ₆ -C ₁₀ aromatic optionally substituted with one or more substituents selected from Rd, optionally with one or more 5- to 10-membered heteroaromatic groups substituted with a substituent selected from Rc and 3 to 12-membered non-aromatic heterocyclic groups optionally substituted with one or more substituents selected from Rc And R ^{24 is} selected from the group consisting of a hydrogen atom and a C ₁ -C ₆ alkyl group optionally substituted with one or more substituents selected from Ra.

[2] The compound or a pharmaceutically acceptable salt thereof according to [1], wherein the aforementioned compound is represented by formula (Ia):

Wherein R ¹ and R ^{2 are} independently selected from the group consisting of C ₁ -C ₆ alkoxy groups, R ^{3 is} selected from the group consisting of halogen atoms, and R ⁶ , R ⁷ and p are as in [1] definition.

[3] The compound or a pharmaceutically acceptable salt thereof according to [1] or [2], wherein R ¹ and R ² are a methoxy group, and R ³ is a chlorine atom.

[4] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [3], wherein p is 1.

[5] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [4], wherein p is 0.

[6] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [5], wherein R ^{7 is a} hydrogen atom.

[7] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [6], wherein R ^{6 is} selected from the group consisting of pyrimidyl, optionally a halogen atom, or C ₁ -C ₆ alkoxy group substituted pyridyl, piperidyl, optionally substituted with a C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group, Optionally substituted by C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group, pyrrolidyl, C ₃ -C ₇ cycloalkyl, tetrahydrofuryl Tetrahydropyranyl, a group consisting of phenyl optionally substituted with a substituent selected from Rb, the group -CH ₂ -Ra and the group -CH ₂ CH ₂ -Ra.

[8] The compound according to any one of [1] to [7], or a pharmaceutically acceptable salt thereof, Ra is independently selected from a hydroxyl group, a C ₁ -C ₆ alkoxy group, and optionally a di ( C ₁ -C ₆ alkyl) amino groups substituted C ₃ -C ₇ cycloalkyl, phenyl optionally substituted with one or more substituents selected from Rd, optionally C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group substituted pyrrolidinyl, optionally via C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl A group consisting of a group-substituted piperidinyl group, a pyridyl group optionally substituted with a halogen atom or a C ₁ -C ₆ alkoxy group, and a thiazolyl group.

[9] The compound according to any one of [1] to [8], or a pharmaceutically acceptable salt thereof, wherein Rb and Rd are independently selected from the group consisting of a halogen atom, a methyl group, and a cyanodimethylamino group (cyano dimethylamino), methoxy, nitro, hydroxy, and trifluoromethyl.

[10] The compound or a pharmaceutically acceptable salt thereof according to any one of [1] to [9], which is selected from the group consisting of 1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopropylmethyl) methylamine; 1- ( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopentyl Methyl) methylamine; 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester; 3-(((((1- (2- (5-chloro-2,4-dimethoxybenzene Propyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) (methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyrrolidine 3-ylmethyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piper Pyridin-4-yl) -N- (cyclohexylmethyl) methylamine; 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester); 1- (1- (2- (5-chloro -2,4-Dimethoxy Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (piperidin-4-ylmethyl) methylamine; N-benzyl-1- (1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-methylbenzyl Methyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) -N- (4-methylbenzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) piperidin-4-yl) -N- (2-fluorobenzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) piperidin-4-yl) -N- (3-fluorobenzyl) methylamine; 1- (1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluorobenzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxybenzyl) Methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl)- N- (2-chlorobenzyl) methylamine; 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-base) Pyridin-4-yl) methyl) amino) methyl) -N, N-dimethylaniline; 3-(((((1- (2- (5-chloro-2,4-dimethoxybenzene Yl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile; 4-((((1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile; 1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2 -Nitrobenzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) -N- (3- (trifluoromethyl) benzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyridin-3-ylmethyl) methylamine; 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyridin-4-ylmethyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((3-fluoro- 4-yl) methyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piper Pyridin-4-yl) -N-((2-methoxypyridin-4-yl) methyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethyl) Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) methylamine; 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N, N -Bis (pyridin-2-ylmethyl) methylamine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) piperidin-4-yl) methyl) cyclobutylamine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridine-7-yl) piperidin-4-yl) methyl) cyclopentylamine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) tetrahydrofuran-3-amine; N-((1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cyclohexylamine; N-((1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) tetrahydro-2H-pyran-4-amine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cycloheptylamine; N- ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyridin-4-yl) methyl) -1-methylpiperidine-4-amine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) piperidin-4-yl) methyl) -1-isopropylpiperidin-4-amine; 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-methylpiperidin-4-yl) methyl) methyl Amine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl ) -2- (1-methylpiperidin-4-yl) ethylamine; N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) piperidin-4-yl) methyl) -N ⁴ , N ⁴ -dimethylcyclohexane-1,4-diamine (N ¹ -((1- ( 2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -N ⁴ , N ⁴ -dimethyl cyclohexane-1,4-diamine ); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(Cyclopropylmethyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidin-3-yl) -N- (cyclopentylmethyl) methylamine; 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a) pyridine-7-yl) pyrrolidin-3-yl) methyl) amino) methyl Methyl) pyrrolidine-1-carboxylic acid tert-butyl ester; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) -N- (pyrrolidin-3-ylmethyl) methylamine; 4-(((((1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (piperidine-4- Methylmethyl) methylamine; N-benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Pyrrolidin-3-yl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) Pyrrolidin-3-yl) -N- (2-fluorobenzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridine-7-yl) pyrrolidin-3-yl) -N- (3-fluorobenzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-fluorobenzyl) methylamine; 4-((((1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N -Dimethylaniline; 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl ) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) phenol; 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-nitrobenzyl) methylamine; 1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (3- (trifluoromethyl ) Benzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine- 3-yl) -N- (4- (trifluoromethyl) benzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) pyrrolidin-3yl) -N- (4-methylbenzyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethyl) Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-chlorobenzyl) methylamine; 1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-chlorobenzyl) methylamine; 1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyridine 3-ylmethyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrole Alk-3-yl) -N- (pyridin-4-ylmethyl) methylamine; 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((3-fluoro-4-yl) methyl) methylamine; 1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-(( 2-fluoro-4-yl) methyl) methylamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) -N, N-bis (pyridin-2-ylmethyl) methylamine; N-((1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-methoxyethylamine; N-((1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cyclobutylamine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-methylpiperidine-4 -Amine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl)- N-((1-methylpiperidin-4-yl) methyl) methylamine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) aniline; and the aforementioned pharmaceutically acceptable salts.

[11] A pharmaceutical composition comprising the compound according to any one of [1] to [10] or a pharmaceutically acceptable salt thereof as an active ingredient.

[12] Use of the pharmaceutical composition according to [11] for treating or preventing cancer.

[13] A pharmaceutical composition according to [12], wherein the cancer is selected from the group consisting of lung cancer, cervical cancer, bladder cancer, esophageal cancer, osteosarcoma, prostate cancer, and soft tissue tumors.

[14] A method for treating or preventing a disease related to SUV39H2 overexpression, comprising administering to a subject in need thereof an effective amount of a compound according to any one of [1] to [10] or a pharmaceutically acceptable compound thereof Accepted salt.

[15] A method according to [14], wherein the aforementioned disease is cancer.

[16] Use of the compound according to any one of [1] to [10] or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for treating or preventing a disease related to SUV39H2 overexpression.

It is an object of the present invention to provide a compound having inhibitory activity on MELK, which is useful for treating a proliferative disease such as cancer, and to provide a pharmaceutical composition comprising the compound. Another object of the present invention is to provide a method for treating and / or preventing a proliferative disease. Yet another object is to provide a process for preparing the compound.

Hereinafter, the compound represented by formula (I) is referred to as compound (I). The same applies to compounds represented by other formula numbers. It must be noted that as used herein and in the scope of the appended patent application, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to a "group" refers to one or more groups unless noted otherwise.

In the definition of each group of the above formula, "C ₁ -C ₆ alkyl" and "C ₁ -C ₆ alkoxy", "C ₁ -C ₆ alkylamino", "di (C ₁ -C ₆ alkyl) amino "," (C ₁ -C ₆ alkyl) carbonyl "," C ₁ -C ₆ alkylthio "," C ₁ -C ₆ alkylsulfinylene "," C sulfonic ₁ -C ₆ alkyl group "and the C ₁ -C ₆ alkyl moiety similar expression refers to a straight or branched chain alkyl group having one to six carbon atoms. Specifically, examples of "C ₁ -C ₆ alkyl" and "C ₁ -C ₆ alkyl moiety" include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl Sec-butyl, tert-butyl, pentyl, 1-methylbutyl, 1-ethylpropyl, 2-methylbutyl ( 2-methylbutyl), isopentyl, tert-pentyl, 1,2-dimethylpropyl, neopentyl, hexyl, 1-methylpentyl, 1-ethylbutyl, 2-methylpentyl, 3-methylpentyl, 4- 4-methylpentyl, isohexyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 1-isopropylpropyl, 1-ethyl-1-methylpropyl , 2,3-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl ), 2-ethylbutyl, and 3-ethylbuty l), but not limited to this.

In this specification, unless otherwise noted, the C ₁ -C ₆ alkyl moiety in each group has the same definition as the “C ₁ -C ₆ alkyl moiety” described above. In the case where the group contains a plurality of C ₁ -C ₆ alkyl moieties, the C ₁ -C ₆ alkyl moieties may be the same or different.

Specific examples of "C ₁ -C ₆ alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, isobutyloxy Tert-butyloxy, butoxy, pentyloxy, and hexyloxy, but not limited thereto.

"C ₁ -C ₆ alkoxycarbonyl" refers to a monovalent group represented by -C (= O) O- (C ₁ -C ₆ alkyl). Specific examples of `` (C ₁ -C ₆ alkoxy) carbonyl '' include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, Isobutyloxycarbonyl, tert-butoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, and hexyloxycarbonyl are not limited thereto.

"(C ₁ -C ₆ alkyl) carbonyl" refers to a monovalent group represented by -C (= O)-(C ₁ -C ₆ alkyl). Specific examples of `` (C ₁ -C ₆ alkyl) carbonyl '' include methylcarbonyl (i.e. acetyl), ethylcarbonyl, propylcarbonyl, isopropylcarbonyl (isopropylcarbonyl), isobutylcarbonyl, tert-butylcarbonyl, butylcarbonyl, pentylcarbonyl, and hexylcarbonyl, but are not limited thereto.

Specific examples of `` C ₁ -C ₆ alkylamino '' include methylamino, ethylamino, propylamino, isopropylamino, butylamino, isopropyl Isobutylamino, sec-butylamino, tert-butylamino, and pentylamino are not limited thereto.

The alkyl portions of the "di (C ₁ -C ₆ alkyl) amino group" may be the same or different. Specific examples of the `` di (C ₁ -C ₆ alkyl) amino group '' include dimethylamino, diethylamino, dipropylamino, diisopropylamine Diisopropylamino, dibutylamino, diisobutylamino, di (sec-butyl) amino, di (tert-butyl) amino (di (tert-butyl) amino), dipentylamino, ethyl (methyl) amino, propyl (methyl) amino, Isopropyl (methyl) amino, butyl (methyl) amino, isobutyl (methyl) amino, Sec-butyl (methyl) amino, tert-butyl (methyl) amino, and pentyl (methyl ) amino), but not limited to this.

Specific examples of the "halogen atom" include fluorine, chlorine, bromine, and iodine atoms.

The term "C ₃ -C ₁₀ cycloalkyl" refers to a saturated monocyclic hydrocarbon group having 3 to 10 carbon atoms and when two or more saturated monocyclic hydrocarbons share two or more carbon atoms The formed bridged cyclic hydrocarbon group has 4 to 10 carbon atoms. The term "C ₃ -C ₁₀ cycloalkyl" also includes cycloalkyl groups that are condensed with aromatic or non-aromatic carbocyclic rings to form a bicyclic group. Specifically, examples of "C ₃ -C ₁₀ cycloalkyl" include saturated monocyclic hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Cycloheptyl and cyclooctyl and bridged hydrocarbon groups, such as, but not limited to, adamantyl.

In the definition of each group of the above formula, "C ₃ -C ₁₀ cycloalkoxy", "(C ₃ -C ₁₀ cycloalkyl) carbonyl", "(C ₃ -C ₁₀ cycloalkyl) sulfonate The definitions of "fluorenyl", "(C ₃ -C ₁₀ cycloalkyl) sulfonamido", and the aforementioned C ₃ -C ₁₀ cycloalkoxy group of similar groups are the same as the above definitions. Specifically, examples of the "C ₃ -C ₁₀ cycloalkoxy group" include cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, cyclohexyloxy, Cycloheptyloxy and cyclooctyloxy, and bridged cyclic hydrocarbyl groups, such as adamantyloxy, are not limited thereto.

The term "C ₆ -C ₁₀ aromatic group" refers to an aromatic carbocyclic group having 6 to 10 carbon atoms and contains an aromatic carbocyclic group that is condensed with an aromatic or non-aromatic carbocyclic ring to form a bicyclic group. group. Specific examples include phenyl, 1-naphthyl, 2-naphthyl, and 2,3-dihydro-1H-indenyl ), But not limited to this.

The term "C ₇ -C ₁₄ aralkyl" refers to an alkyl group substituted with an aromatic group having 7 to 14 carbon atoms. Specific examples include benzyl, 2-phenylethyl, 1-phenylethyl, naphtha-1-ylmethyl, naphtha-1-ylmethyl, Naphtha-2-ylmethyl and naphtha-2-ylmethyl and 2,3-dihydro-1H-inden-4-ylmethyl, but Not limited to this.

In the definition of each group of the above formula, the definitions of the "C ₇ -C ₁₄ aralkylsulfonyl group" and the C ₇ -C ₁₄ aralkyl portion of the aforementioned similar group are the same as the above definitions. Specifically, examples of the "C ₇ -C ₁₄ aralkylsulfonyl group" include, but are not limited to, benzylsulfonyl.

The term "5- to 10-membered heteroaromatic group" refers to an aromatic heterocyclic group having one or more heteroatoms, preferably one to three heteroatoms, and the heteroatoms are selected from the group consisting of nitrogen, oxygen, and sulfur atoms. group. The term "5- to 10-membered heteroaromatic group" includes an aromatic heterocyclic group that is condensed with an aromatic or non-aromatic carbocyclic ring, or an aromatic or non-aromatic heterocyclic ring to form a bicyclic group, and also includes Either a non-aromatic carbocyclic group, or an aromatic carbocyclic group that is condensed to form a bicyclic group. Specific examples include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolyl, Oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridyl Pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophenyl, benzoxazolyl , Benzothiazolyl, isoindolyl, indolyl, 1H-indazolyl, benzimidazolyl, benzotriazolyl ), Oxazolopyrimidinyl, thiazolopyrimidinyl, pyrrolopyridinyl, pyrrolopyrimidinyl, imidazopyridinyl, purinyl, quinolinyl (quinolinyl), isoquinolinyl Cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pyridopyrimidinyl, [1,2,4 ] Triazolo [1,5-a] pyridyl ([1,2,4] triazolo [1,5-a] pyridyl) and pyrrolo [2,3-b] pyridyl (pyrrolo [2,3- b] pyridyl), but is not limited to this. In particular, thienyl, pyrrolyl, imidazolyl, isoxazolyl, pyridyl, pyrimidyl, pyrazolyl, 1H-indazolyl, benzimidazolyl, [1,2,4] triazole Ac [1,5-a] pyridyl or pyrrolo [2,3-b] pyridyl.

The term "3 to 12-membered non-aromatic heterocyclic group" refers to a non-aromatic heterocyclic group having one or more heteroatoms, preferably one to three heteroatoms, the heteroatoms being selected from the group consisting of nitrogen, oxygen, and sulfur A group of atoms. The term "3- to 12-membered non-aromatic heterocyclic group" includes non-aromatic heterocyclic groups that are condensed with an aromatic or non-aromatic carbocyclic ring or an aromatic or non-aromatic heterocyclic ring to form a bicyclic group, and also A non-aromatic carbocyclic group that condenses with an aromatic or non-aromatic heterocyclic ring to form a bicyclic group. Specific examples include aziridinyl, azetidinyl, pyrrolidinyl, piperidyl (including piperidino), azetidinyl Alkyl (azepanyl), 1,2,5,6-tetrahydropyridyl (1,2,5,6-tetrahydropyridyl), 1,2,3,6-tetrahydropyridyl (1,2,3,6) -tetrahydropyridyl), imidazolidinyl, pyrazolidinyl, piperazinyl, homopiperazinyl, pyrazolinyl, oxiranyl , Tetrahydrofuranyl, tetrahydro-2H-pyranyl, 5,6-dihydro-2H-pyranyl, oxazolidine Oxazolidinyl, morpholinyl (including morpholino), tetrahydrothiophenyl, tetrahydro-2H-thiopyranyl, thiooxazolyl (thioxazolidinyl), thiomorpholinyl, 2H-oxazolyl, 2H-thioxazolyl, dihydroindolyl, dihydroisodiyl Dihydroisoindolyl Dihydrobenzofuranyl, benzoimidazolidinyl, 2,3-dihydrobenzimidazolyl, 2,3-dihydrobenzimidazolyl (2 , 3-dihydrobenzoxazolyl, dihydrobenzothioxazolyl, benzodioxolinyl, tetrahydroquinolyl, tetrahydroisoquinolyl, dihydro-2H -Dihydro-2H-chromanyl, dihydro-1H-dihydro-1H-chromanyl, dihydro-2H-thioanyl -thiochromanyl), dihydro-1H-thiochromanyl, tetrahydroquinoxalinyl, tetrahydroquinazolinyl, dihydrobenzodioxanyl (dihydrobenzodioxanyl), oxetanyl, 1,2-dihydropyridyl (1,2-dihydropyridyl), 1-azabicyclo [2.2.2] oct-3-yl (1-azabicyclo [ 2.2.2] octan-3-yl), 2,5-azabicyclo [2.2.1] heptyl (2,5-azabicyclo [2.2.1] heptyl), 8-azabicyclo [3.2.1] octyl (8-azabicyclo [3.2.1] octyl), piperidine-4-spiro 3'-pyridine 1-yl (piperidin-4-spiro-3'-pyrrolidin-1-yl) and isoindolyl (isoindolyl), but is not limited thereto. In particular, azetidinyl, pyrrolidinyl, piperidino, piperidinyl, piperazinyl, morpholino, morpholinyl, 1,2-dihydropyridyl, 1,2 , 5,6-tetrahydropyridyl, 1-azabicyclo [2.2.2] oct-3-yl, 2,5-azabicyclo [2.2.1] heptyl, 8-azabicyclo [3.2.1 ] Octyl, 2,3-dihydrobenzimidazolyl or piperidin-4-spiro-3'-pyrrolidin-1-yl.

The term "3 to 12 member nitrogen-containing heterocyclic group" means an aromatic or non-aromatic heterocyclic group having one nitrogen atom and one or more additional heteroatoms, preferably one to three heteroatoms, and the heteroatoms are selected from the group consisting of A group of nitrogen, oxygen, and sulfur atoms. The term "3- to 12-membered nitrogen-containing heterocyclic group" includes a heterocyclic group that is condensed with an aromatic or non-aromatic carbocyclic ring, or an aromatic or non-aromatic heterocyclic ring to form a bicyclic group. Specific examples include aziridinyl, azetidinyl, pyrrolyl, pyrrolidinyl, piperidinyl (including piperidino), azetidinyl, imidazolyl, pyrazolyl, triazolyl , Tetrazolyl, piperazinyl, and morpholinyl.

The term "C ₁ -C ₆ alkylene" refers to a straight or branched chain divalent group having 1 to 6 carbon atoms, and contains C ₁ -C ₄ alkylene and C ₁ -C ₃ alkylene . The foregoing examples include -CH _2- , -CH (CH ₃ )-, -CH (CH ₂ CH ₃ )-, -CH ₂ CH _2- , -CH (CH ₃ ) CH _2- , and -CH ₂ CH (CH ₃ )-.

For example, formula (I) refers to the following structure.

Examples of Q include -CH _2- , -CH (CH ₃ )-, -CH (CH ₂ CH ₃ )-, -CH ₂ CH _2- , -CH (CH ₃ ) CH _2- , and -CH ₂ CH (CH ₃ )-.

The pharmaceutically acceptable salt of the compound (I) means, for example, a pharmaceutically acceptable acid-added salt, amino acid-added salt, or the like. Specific examples of the pharmaceutically acceptable acid addition salt of the compound (I) include inorganic acid salts such as hydrochloride, sulfate and phosphate, and organic acid salts such as acetate , Maleate, fumarate, citrate, and similar organic salts described above, and examples of pharmaceutically acceptable amino acid addition salts include, for example, lysine (lysine), glycine, phenylalanine, asparagine acid or glutamic acid addition salt. In particular, the pharmaceutically acceptable salts of the compound (I) include hydrochloride, dihydrochloride salt, and trihydrochloride salt.

Examples of diseases that overexpress SUV39H2 can be treated and / or prevented by a pharmaceutical composition comprising the compound of the present invention or a pharmaceutically acceptable salt thereof as an active ingredient, including cancer, breast cancer, Bladder cancer, cervical cancer, cholangiocellular carcinoma, chronic myeloid leukemia (CML), colorectal cancer, endometriosis ( endometriosis, esophagus cancer, gastric cancer, liver cancer, non-small cell lung cancer (NSCLC), lymphoma, osteosarcoma, ovary Cancer (ovarian cancer), pancreatic cancer (prostate cancer), renal cancer (renal cancer) and small cell lung cancer (SCC) are not limited thereto. Examples of treatable and / or preventable cancers include breast cancer, bladder cancer, cervical cancer, bile duct cancer, chronic myelogenous leukemia, colorectal cancer, endometriosis, esophageal cancer, gastric cancer, liver cancer, non-small Cell lung cancer, lymphoma, osteosarcoma, ovarian cancer, pancreatic cancer, prostate cancer, kidney cancer, and small cell lung cancer, but are not limited thereto. In one embodiment, examples of cancer include lung cancer, cervical cancer, bladder cancer, esophageal cancer, osteosarcoma, prostate cancer, and soft tissue tumors.

Compound (I) includes compounds which may have stereoisomers, such as regioisomers, geometrical isomers, optical isomers, and tautomers ), And all possible isomers and mixtures thereof including them are included in the present invention.

Compound (I) also includes compounds having one or more secondary stable isotopes or radioisotopes, such as ² H, ³ H, ¹³ C, ¹⁴ C, ¹⁵ N, ¹⁸ O, and similar isotopes, which may be used in the preparation of compounds having a Ordinary procedures for one or more of the above-mentioned isotopic compounds are consistent.

Furthermore, the compound (I) and a pharmaceutically acceptable salt thereof may exist in the form of solvates with water (hydrate) or various other solvents, and these solvates are also included in the present invention.

Specific examples of the compound (I) of the present invention are shown in Table 1-1 (Examples 1 to 68). However, the compound of the present invention is not limited thereto.

Specific examples of the compound (I) of the present invention are also shown in Table 1-2 (Examples 2-1 to 2-119). However, the compound of the present invention is not limited thereto.

Compound (I) and its pharmaceutically acceptable salts may be administered alone; however, generally, it is desirable to provide them in various types of pharmaceutical formulations. Such pharmaceutical formulations are used in animals or humans.

The pharmaceutical formulation of the present invention may contain only the compound (I) or a pharmaceutically acceptable salt thereof, or a mixture together with any other active ingredient for treatment as an active ingredient. Furthermore, by any method well known in the technical field of pharmaceutical formulation, by combining the active ingredient with one or more types of pharmaceutically acceptable carriers such as diluent, solvent and excipients ( excipient)) to prepare these pharmaceutical formulations.

Desirably, the most effective route of administration is for treatment, and examples include an oral route or a parenteral route, such as an intravenous route.

Administration forms are, for example, tablets and injections.

Tablets are suitable for oral administration, and excipients such as lactose, disintegrants such as starch, lubricants such as magnesium stearate, and binders such as hydroxypropyl may be used Hydroxypropylcellulose to make tablets.

Injections are suitable for parenteral administration, and injections can be prepared using, for example, solvents or diluents, such as saline solutions, glucose solutions or mixtures of saline and glucose solutions.

The dose and number of times of Compound (I) or a pharmaceutically acceptable salt thereof vary depending on the administration form, the age and weight of the patient, the nature or severity of the symptoms to be treated, etc., but generally for oral administration, adults 0.01 mg to 1000 mg, preferably 0.05 mg to 100 mg, and administered once to several times a day. In the case of parenteral administration, such as intravenous administration, it is administered once to several times a day to an adult in an amount of 0.001 mg to 1000 mg, or preferably 0.01 mg to 100 mg. However, these doses and the number of doses vary depending on the various conditions described above.

Unless otherwise stated, the intermediates and target compounds in the following examples can be separated and purified by subjecting them to isolation and purification methods commonly used in synthetic organic chemistry, and examples include filtration, extraction, washing, drying, and concentration , Recrystallization and various types of chromatography. Alternatively, the intermediate may be subjected to the next reaction without purification.

Hereinafter, the present invention is specifically described through examples, but the scope of the present invention should not be construed as being limited thereto.

Furthermore, in the examples shown below, unless otherwise specified, if the defined group is changed or is not suitable for this method under the conditions of the preparation method, it can be used by introduction commonly used in synthetic organic chemistry. And removal of protecting groups (for example, "Protective Groups in Organic Synthesis", TW Greene, John Wiley & Sons Inc., 1999) to prepare the target compound. The order of the reaction steps, such as the introduction of substituents, can be changed as needed.

Examples

Abbreviation

Experiment

Unless otherwise noted, use reagents and solvents received from commercial suppliers. Proton nuclear magnetic resonance spectra were obtained on a Bruker AVANCE 300 spectrometer at 300 MHz, on a Bruker AVANCE 400 spectrometer at 400 MHz, or on a Bruker AVANCE 500 spectrometer at 500 MHz. Tetramethylsilane was used as an internal standard for the proton spectrum. A Merck TLC silica-gel 60F ₂₅₄ (Merck TLC silica-gel 60F ₂₅₄ ) disc was used for thin-layer chromatography. Visualization of TLC discs was performed using UV light (254 nm). Mass spectra were obtained on a Shimadzu LCMS-2010EV spectrometer using electrospray ionization or atmospheric pressure chemical ionization. HPLC analysis was performed using Method 1 to Method 8.

HPLC method 1

Column: Eclipse XDB C18 (4.6 × 150mm, 5.0μm)

Column temperature: ambient

Detection: UV @ 220nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC method 2

Column: Eclipse XDB C18 (4.6 × 150mm, 5.0μm)

Column temperature: ambient

Detection: UV @ 230nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC method 3

Column: Eclipse XDB C18 (4.6 × 150mm, 5.0μm)

Column temperature: ambient

Detection: UV @ 254nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC method 4

Column: Eclipse plus-c18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 220nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC method 5

Column: Eclipse plus-c18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 254nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 6

Column: Zorbax SB-CN (4.6 × 1500mm, 5μm)

Column temperature: ambient

Detection: UV @ 254nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 7

Column: Xbridge-c18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 220nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC method 8

Column: Zodiac-c18 (4.6 × 100mm, 3.0μm)

Column temperature: ambient

Detection: UV @ 220nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 9

Column: XBridge C18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 220nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 10

Column: Eclipse plus-c18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 240nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 11

Column: Atlantis T3 C18 (4.6 × 150mm, 3.0μm)

Column temperature: ambient

Detection: UV @ 220nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 12

Column: Eclipse plus-c18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 220nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 13

Column: Eclipse plus-c18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 254nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 14

Column: Eclipse plus-c18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 254nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 15

Column: Eclipse plus-c18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 215nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

HPLC Method 16

Column: XBridge C18 (4.6 × 100mm, 3.5μm)

Column temperature: ambient

Detection: UV @ 254nm

Sample diluent: acetonitrile: H ₂ O (50:50)

Mobile phase A: water (with 0.05% TFA)

Mobile phase B: acetonitrile (with 0.05% TFA)

Preparation of 1- (5-chloro-2,4-dimethoxyphenyl) ethanone (1- (5-chloro-2,4-dimethoxyphenyl) ethanone) 2

KCl was added to a solution of 1- (2,4-dimethoxyphenyl) ethanone (1- (2,4-dimethoxyphenyl) ethanone) 1 (40 g, 222 mmol) in acetonitrile (500 mL) and water (500 mL). (18.2 g, 242 mmol), then Oxone ^™ (150 g, 242 mmol) was added, and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with EtOAc (1 L), and the organic layer was separated, washed with brine (500 mL), dried over anhydrous Na ₂ SO ₄ , filtered, and concentrated under reduced pressure. The obtained solid was triturated with hexane, filtered and dried under vacuum to give 1- (5-chloro-2,4-dimethoxyphenyl) ethanone 2 (30.5 g, 64%) as white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 7.87 (s, 1H), 6.47 (s, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 2.56 (s, 3H). ESI + APCI-MS m / z 215 [M + H] ⁺ .

Preparation of 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone (2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone) 3

A solution of 1- (5-chloro-2,4-dimethoxyphenyl) ethanone 2 (30.0 g, 140 mmol) in CH ₂ Cl ₂ / CH ₃ OH (700 mL / 150 mL) (portion- wise) tetrabutylammonium tribromide (TBATB, 67.6 g, 140 mmol) was added for 1 hour, and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure until the volume was reduced to 20%, and then the product precipitated as a pale yellow solid. The solid was triturated with cold methanol, filtered and dried under vacuum to give the desired 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 3 (37 g, 90%) as Off-white solid.

¹ H NMR (400 MHz, CDCl ₃ ): δ 7.93 (s, 1H), 6.48 (s, 1H), 4.52 (s, 2H), 3.98 (s, 6H). ESI + APCI-MS m / z 293 [M] ⁺ .

((1- (2-amino-4-yl) piperidin-4-yl) methyl) carbamic acid tert-butyl (tert -butyl ((1- (2 -aminopyridin-4-yl) piperidin- Preparation of 4-yl) methyl) carbamate) 4

For 2-amino-4-chloropyridine (2.50 g, 19.5 mmol) in a mixture of isopropanol and N , N' -diisopropylethylamine (50 mL / 25 mL) solution, placed in a sealed tube was added (piperidin-4-ylmethyl) carbamic acid tert-butyl ester (tert -butyl (piperidin-4- ylmethyl) carbamate) (6.30g, 29.4mmol). The tube was sealed and the reaction mixture was heated at 120 ° C for 24 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure, and then the residue was partitioned between EtOAc and a saturated NaHCO ₃ solution (300 mL: 100 mL). The layers were separated, and the EtOAc layer was washed with brine (100 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated under reduced pressure to give the crude product. The product was triturated with hexane, filtered under vacuum and dried to give (1- (2-aminopyridin-4-yl) piperidin-4-yl) methyl) aminocarboxylic acid tert-butyl ester 4 (5.5g , 92%), as an off-white solid, which was used in the next step without further purification. ESI + APCI-MS m / z 307 [M + H] +.

((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino tert-butyl (tert -butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-4-yl) methyl) carbamate) Preparation of 5

(1- (2-Aminopyridin-4-yl) piperidin-4-yl) methyl) t-butylaminocarbamate 4 (5.0 g, 16.3 mmol) and 2 in acetone (200 mL) A mixture of bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 3 (5.3 g, 18.1 mmol) was heated at 75 ° C for 16 hours. The reaction mixture was cooled to room temperature and a white precipitate formed. The precipitate was collected by vacuum filtration, washed with hexane (200 mL), and dried to give (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridin-7-yl) piperidin-4-yl) methyl) t-butyl hydrocarbamate 5 hydrobromide (7.1 g, 79%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 13.13 (br s, 1H), 8.49 (d, J = 7.8Hz, 1H), 8.23 (s, 1H), 7.91 (s, 1H), 7.29 (d , J = 6.0Hz, 1H), 6.98-6.92 (m, 2H), 6.66 (s, 1H), 4.05-3.98 (m, 8H), 3.03 (t, J = 12.6Hz, 2H), 2.85 (t, J = 5.4Hz, 2H), 1.75 (d, J = 11.7Hz, 3H), 1.38 (s, 9H), 1.23-1.14 (m, 2H); HPLC (Method 1) 99.2% (area under the curve), t _R = 13.78 minutes; ESI + APCI-MS m / z 501 [M + H] ⁺ .

Preparation of (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methylamine 6

(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine in CH ₂ Cl ₂ (30 mL) A solution of tert-butyl 4-methyl) methyl) carbamate 5 (3.00 g, 5.98 mmol), and a solution of HCl (4.0 M in 1,4-dioxane, 30 mL) was added. The reaction mixture was stirred at room temperature for 16 hours. The solid obtained in the reaction was collected by vacuum filtration and washed with CH ₂ Cl ₂ (100 mL). The solid was then suspended in water (70 mL) and basified to pH 10 with a saturated sodium bicarbonate solution (70 mL), and then a pale yellow solid precipitated. The solid was collected by vacuum filtration, washed with water and dried to give (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methylamine 6 (2.1 g, 87%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H) 6.77 (d, J = 6.0Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.4Hz, 2H), 2.87 (t, J = 2.0Hz, 2H ), 2.70 (t, J = 11.6Hz, 2H), 1.74-1.58 (m, 3H), 1.24-1.16 (m, 2H); ESI + APCI-MS m / z 401 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2,2-dimethylpropan-1-amine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin- Preparation of 4-yl) methyl) -2,2-dimethylpropan-1-amine) 8a

For (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- in CH ₃ OH (5 mL)- A suspension of 4-yl) methylamine 6 (150 mg, 0.37 mmol) and pivalaldehyde (48 mL, 0.56 mmol) was added with acetic acid (0.1 mL), and the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (118 mg, 1.87 mmol) was added thereto, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate (20 mL), and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated under reduced pressure to give the crude product. The product was purified by combi-flash chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)]. The product-containing fractions were combined and concentrated in vacuo to give N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) piperidin-4-yl) methyl) -2,2-dimethylprop-1-amine 8a (70 mg, 39%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.77 (dd, J = 2.4,7.6Hz, 1H), 6.63 (d, J = 2Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.4Hz, 2H), 2.74-2.67 (m, 2H), 2.52-2.48 (m, 2H), 2.34-2.30 (m, 2H), 1.81 (d, J = 11.2Hz, 2H), 1.64 (br s, 1H), 1.27-1.15 (m, 2H), 0.89 (s, 9H); HPLC (method 1) 98.9% (area under the curve), t _R = 12.15 minutes; ESI + APCI-MS m / z 471 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of cyclopropylmethyl) methylamine 8b (Example 3)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (cyclopropylmethyl) methanamine 8b, and to obtain an off-white solid (18% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.4,7.6Hz, 1H), 6.64 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.79 (d, J = 12.4Hz, 2H), 2.74-2.68 (m, 2H ), 2.52-2.48 (m, 4H), 1.80 (d, J = 12.0Hz, 2H), 1.64 (br s, 1H), 1.28-1.17 (m, 2H), 0.95-0.87 (m, 1H), 0.45 -0.40 (m, 2H), 0.14-0.10 (m, 2H); HPLC (Method 5) 95.0% (area under the curve), t _R = 6.36 minutes; ESI + APCI-MS m / z 455 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of cyclopentylmethyl) methylamine 8c (Example 4)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (cyclopentylmethyl) methanamine 8c, and to obtain an off-white solid (45% yield).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.5Hz, 1H), 8.16 (s, 1H), 8.00 (s, 1H), 6.86 (s, 1H), 6.79 (d, J = 7.5Hz, 1H), 6.65 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.80 (d, J = 12.0Hz, 2H), 2.77-2.64 (m, 6H), 2.12-1.98 (m, 1H), 1.84-1.70 (m, 5H), 1.57-1.49 (m, 4H), 1.31-1.17 (m, 4H); HPLC (Method 1) 96.0% (area under the curve), t _R = 12.31 minutes; ESI + APCI-MS m / z 483 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl Tert-butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) pyrrolidine-1-carboxylate) 8d (Example 5)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 8d, obtained as an off-white solid (15% yield rate).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.4,7.6Hz, 1H), 6.62 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.4Hz, 2H), 3.39- 3.35 (m, 1H), 3.28-3.26 (m, 2H), 3.20-3.11 (m, 1H), 2.93-2.89 (m, 1H), 2.73-2.67 (m, 2H), 2.52-2.48 (m, 1H) ), 2.41 (d, J = 6.0Hz, 2H), 2.26-2.20 (m, 1H), 1.94-1.86 (m, 1H), 1.79 (d, J = 11.6Hz, 2H), 1.64-1.47 (m, 2H), 1.39 (s, 9H), 1.24-1.18 (m, 2H); HPLC (Method 4) 98.3% (area under the curve), t _R = 12.39 minutes; ESI + APCI MS m / z 584 [M + H ] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 9 (Example 6)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) (methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 9 and obtained as an off-white solid (10% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.12 (d, J = 7.6Hz, 1H), 8.05 (s, 1H), 7.96 (s, 1H), 6.79 (s, 1H), 6.77 (d, J = 2.0Hz, 1H), 6.66 (s, 1H), 4.02 (s, 3H), 3.95 (s, 3H), 3.84 (d, J = 14.8Hz, 2H), 3.49-3.43 (m, 1H), 3.44 -3.36 (m, 2H), 3.06-3.02 (m, 1H), 2.81 (t, J = 12.4Hz, 2H), 2.45-2.39 (m, 1H), 2.33-2.31 (m, 2H), 2.26-2.20 (m, 4H), 2.04-1.88 (3H), 1.78-1.69 (m, 1H), 1.66-1.58 (m, 1H), 1.45 (s, 10H), 1.34-1.28 (m, 2H); HPLC (method 1) 91.3% (area under the curve), t _R = 12.32 minutes; ESI + APCI-MS m / z 598 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of pyrrolidin-3-ylmethyl) methylamine 8e (Example 7)

3-((((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) in 2,2,2-trifluoroethanol (3.0 mL) at 0 ° C [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 8d (100 mg) solution was added trimethylsilane Trimethylsilyl chloride (0.1 mL), and stirred at the same temperature for 30 minutes. The reaction mixture was evaporated to dryness under reduced pressure and washed with hexane to give 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine 7-yl) piperidin-4-yl) - N - hydrochloride (pyrrolidin-3-yl) methylamine 8e, (25mg, 30%), as an off-white solid.

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 13.83 (brs, 1H), 9.41-9.17 (m, 4H), 8.52 (d, J = 7.6 Hz, 1H), 8.25 (s, 1H), 8.08 ( s, 1H), 7.32 (dd, J = 2.0, 7.6 Hz, 1H), 6.97 (s, 1H), 6.78 (d, J = 2.0 Hz, 1H), 4.05 (br s, 5H), 3.98 (s, 3H), 3.40-3.36 (m, 1H), 3.28-3.20 (m, 1H), 3.14-2.98 (m, 6H), 2.88-2.82 (m, 2H), 2.78-2.70 (m, 1H), 2.17- 2.09 (m, 2H), 1.98-1.94 (m, 2H), 1.75-1.69 (m, 1H), 1.33-1.25 (m, 2H); HPLC (Method 1) 93.9% (area under the curve), t _R = 11.07 minutes; ESI + APCI-MS m / z 484 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( Preparation of cyclohexylmethyl) methylamine 8f (Example 8)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (cyclohexylmethyl) methanamine 8f, and to obtain an off-white solid (38% yield).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.5Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.77 (d, J = 7.2Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.3Hz, 2H), 2.71 (t, J = 10.8Hz, 2H), 2.40 (d, J = 6.6 Hz, 2H), 1.82-1.64 (m, 9H), 1.41-1.09 (m, 7H), 0.92-0.81 (m, 2H); HPLC (method 1) 94.8% ( Area under the curve), t _R = 12.55 minutes; ESI + APCI-MS m / z 497 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester) 8 g (Example 9)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a to prepare 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazolo [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester) 8 g, obtained as an off-white solid (36% Yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.79 (dd, J = 2.0, 7.6 Hz, 1H), 6.65 (d, J = 2.0 Hz, 1H), 4.00 (s, 3H), 3.93 (br s, 5H), 3.80 (d, J = 12.4 Hz, 2H), 2.75 -2.66 (m, 4H), 2.59 (br s, 3H), 1.81 (d, J = 13.2Hz, 2H), 1.70 (d, J = 11.2Hz, 4H), 1.39 (s, 9H), 1.29-1.22 (m, 3H), 1.04-0.97 (m, 2H); HPLC (Method 6) 95.0% (area under the curve), t _R = 13.86 minutes; ESI + APCI-MS m / z 598 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( Preparation of piperidin-4-ylmethyl) methylamine 8h (Example 10)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl)- N- (pyrrolidin-3-ylmethyl) methylamine 8e was prepared in the same manner as 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridin-7-yl) piperidin-4-yl) - N - (piperidin-4-yl) methylamine 8h, and to obtain an off-white solid (18% yield).

¹ H NMR (300 MHz, DMSO- d ₆ ): δ 13.91 (br s, 1H), 9.08-8.68 (m. 4H), 8.53 (d, J = 7.5 Hz, 1H), 8.25 (s, 1H), 8.10 (s, 1H), 7.32 (d, J = 6.3Hz, 1H), 6.97 (s, 1H), 6.79 (s, 1H), 4.05 (br s, 5H), 3.98 (s, 3H), 3.30-3.24 (m, 2H), 3.10-3.02 (m, 2H), 2.85 (br s, 6H), 2.16-2.06 (m, 2H), 1.98-1.94 (m, 4H), 1.49-1.23 (m, 4H); HPLC (method 2) 96.8% (AUC), t _R = 11.05 minutes; ESI + APCI-MS m / z 498 [m + H] +.

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Preparation of methylamine 8i (Example 11)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl)) Imidazolo [1,2-a] pyridin-7-yl) piperidin-4-yl) methylamine 8i was obtained as an off-white solid (26% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 7.34-7.28 (m, 4H), 7.22- 7.19 (m, 1H), 6.86 (s, 1H), 6.77 (d, J = 6.4Hz, 1H), 6.62 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.77 (d , J = 12.4Hz, 2H), 3.69 (s, 2H), 2.73-2.67 (m, 2H), 2.39 (d, J = 6.0Hz, 2H), 1.81 (d, J = 12.0Hz, 2H), 1.61 (br s, 1H), 1.26-1.17 (m, 2H); HPLC (method 6) 99.3% (area under the curve), t _R = 13.61 minutes; ESI + APCI-MS m / z 491 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( 2-methylbenzyl) methylamine (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl)- Preparation of N- (2-methylbenzyl) methanamine) 8j (Example 12)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (2- methylbenzyl) methylamine 8j, and obtained (12% yield) as an off white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.34-7.32 (m, 1H), 7.14- 7.12 (m, 3H), 6.86 (s, 1H), 6.78 (dd, J = 2.4, 7.6Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.79 (d, J = 12.4Hz, 2H), 3.71 (s, 2H), 2.75-2.69 (m, 2H), 2.45 (d, J = 6.0Hz, 2H), 2.30 (s, 3H), 1.83 (d, J = 12.4Hz, 2H), 1.67 (br s, 1H), 1.28-1.20 (m, 2H); HPLC (Method 4) 95.8% (area under the curve), t _R = 12.47 minutes; ESI + APCI-MS m / z 505 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 4-methylbenzyl) methylamine 8k (Example 13)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (4- methylbenzyl) methylamine 8k, and to obtain an off-white solid (13% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.05 (d, J = 7.6Hz, 1H), 7.95 (s, 1H), 7.88 (s, 1H), 7.22 (d, J = 8.0Hz, 2H), 7.13 (d, J = 8.0Hz, 2H), 6.70 (s, 1H), 6.68 (d, J = 2.4Hz, 1H), 6.58 (d, J = 2.4Hz, 1H), 3.93 (s, 3H), 3.88 (s, 2H), 3.86 (s, 3H), 3.78 (d, J = 13.2Hz, 2H), 2.77-2.71 (m, 2H), 2.67 (d, J = 6.4Hz, 2H), 2.25 (s , 3H), 1.81-1.78 (m, 3H), 1.33-1.24 (m, 2H); HPLC (method 6) 93.4% (area under the curve), t _R = 11.72 minutes; ESI + APCI-MS m / z 505 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 2-fluorobenzyl) methylamine 8l (Example 14)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (2- fluorobenzyl) methylamine 8l, and obtained (10% yield) as an off white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.50-7.46 (m, 1H), 7.29- 7.25 (m, 1H), 7.18-7.11 (m, 2H), 6.86 (s, 1H), 6.78 (dd, J = 2.4,8.0Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H) , 3.93 (s, 3H), 3.78 (d, J = 12.8Hz, 2H), 3.74 (s, 2H), 2.74-2.66 (m, 2H), 2.42 (d, J = 6.4Hz, 2H), 1.82 ( d, J = 12.4Hz, 2H), 1.62 (br s, 1H), 1.26-1.20 (m, 2H); HPLC (Method 4) 99.7% (area under the curve), t _R = 12.16 minutes; ESI + APCI- MS m / z 509 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 3-fluorobenzyl) methylamine 8m (Example 15)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (3- fluorobenzyl) methylamine 8m, and to obtain an off-white solid (13% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.36-7.31 (m, 1H), 7.18- 7.15 (m, 2H), 7.05-7.00 (m, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.0,7.6Hz, 1H), 6.62 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.8Hz, 2H), 3.71 (s, 2H), 2.73-2.67 (m, 2H), 2.38 (d, J = 6.8Hz, 2H), 1.82 (d, J = 11.2Hz, 2H), 1.61 (br s, 1H), 1.27-1.20 (m, 2H); HPLC (method 5) 99.5% (area under the curve), t _R = 6.63 minutes ; ESI + APCI-MS m / z 509 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 4-fluorobenzyl) methylamine 8n (Example 16)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (4- fluorobenzyl) methylamine 8n, and obtain (8% yield) as an off white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.38-7.34 (m, 2H), 7.14- 7.09 (m, 2H), 6.86 (s, 1H), 6.78 (dd, J = 2.4, 8.0Hz, 1H), 6.62 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s , 3H), 3.77 (d, J = 12.4Hz, 2H), 3.67 (s, 2H), 2.73-2.66 (m, 2H), 2.38 (d, J = 6.8Hz, 2H), 1.81 (d, J = 12.0Hz, 2H), 1.61 (br s, 1H), 1.26-1.19 (m, 2H); HPLC (method 5) 98.9% (area under the curve), t _R = 6.49 minutes; ESI + APCI-MS m / z 509 [M + H] +.

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( Preparation of 4-methoxybenzyl) methylamine 8o (Example 17)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (4- methoxybenzyl) methylamine 8o, and to obtain an off-white solid (8% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.24 (d, J = 8.8Hz, 2H) , 6.87-6.85 (m, 3H), 6.77 (dd, J = 2.4, 7.6 Hz, 1H), 6.62 (d, J = 2.0 Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.77 (d, J = 12.8Hz, 2H), 3.72 (s, 3H), 3.63 (s, 2H), 2.73-2.67 (m, 2H), 2.38 (d, J = 6.8Hz, 2H), 1.80 (d , J = 12.0Hz, 2H), 1.60 (br s, 1H), 1.25-1.17 (m, 2H); HPLC (method 4) 97.2% (area under the curve), t _R = 12.05 minutes; ESI + APCI-MS m / z 521 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 2-chlorobenzyl) methylamine 8p (Example 18)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (2- chlorobenzyl) methylamine 8p, and obtained (10% yield) as an off white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.55 (dd, J = 1.2, 7.6Hz, 1H), 7.40 (dd, J = 1.2, 8.0 Hz, 1H), 7.34-7.30 (m, 1H), 7.28-7.23 (m, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.4, 7.6Hz, 1H), 6.63 (d, J = 1.6Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.80-3.78 (m, 4H), 2.75-2.69 (m, 2H), 2.44 (d, J = 6.4 Hz, 2H), 1.83 (d, J = 12.0 Hz, 2H), 1.64 (br s, 1H), 1.28-1.20 (m, 2H); HPLC (method 4) 99.1% (curve Lower area), t _R = 12.44 minutes; ESI + APCI-MS m / z 526 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -N , N -dimethylaniline 8q (Example 19)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a to prepare 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazolo [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) -N , N -dimethylaniline 8q and obtained as an off-white solid (6% yield ).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.14 (d, J = 8.8Hz, 2H) , 6.86 (s, 1H), 6.77 (dd, J = 2.0, 7.6Hz, 1H), 6.66 (d, J = 8.8Hz, 2H), 6.62 (s, 1H), 4.00 (s, 3H), 3.93 ( s, 3H), 3.77 (d, J = 12.0Hz, 2H), 3.57 (s, 2H), 2.85 (s, 6H), 2.73-2.67 (m, 2H), 2.37 (d, J = 6.8Hz, 2H ), 1.80 (d, J = 11.6 Hz, 2H), 1.60 (br s, 1H), 1.24-1.16 (m, 2H); HPLC (method 5) 94.75% (area under the curve), t _R = 6.43 minutes; ESI + APCI-MS m / z 534 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) benzonitrile (3-((((((1- (2- (5- (chloro), 4-dimethoxyphenyl) imidazo [1,2-a) pyridin-7-yl) piperidin- Preparation of 4-yl) methyl) amino) methyl) benzonitrile) 8r (Example 20)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile 8r, and obtained as an off-white solid (9% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.79 (s, 1H), 7.69 (dd, J = 1.6, 8.0 Hz, 2H), 7.52 (t, J = 7.6 Hz, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.4, 7.6 Hz, 1H), 6.62 (d, J = 2.0 Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.8Hz, 2H), 3.75 (s, 2H), 2.74-2.66 (m, 2H), 2.38 (d , J = 6.4Hz, 2H), 1.82 (d, J = 11.2Hz, 2H), 1.62 (br s, 1H), 1.26-1.18 (m, 2H); HPLC (method 5) 97.1% (area under the curve) , T _R = 6.59 minutes; ESI + APCI-MS m / z 516 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) benzonitrile (4-((((((1- Preparation of 4-yl) methyl) amino) methyl) benzonitrile) 8s (Example 21)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a to prepare 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazolo [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile 8s and obtained as an off-white solid (8% yield).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.5Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.78 (d, J = 7.8Hz, 2H) , 7.55 (d, J = 7.8Hz, 2H), 6.86 (s, 1H), 6.78 (d, J = 7.2Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.80-3.72 (m, 4H), 2.75-2.67 (m, 2H), 2.39 (d, J = 6.0Hz, 2H), 1.82 (d, J = 12.0Hz, 2H), 1.62 (br s, 1H), 1.27-1.17 (m, 2H); HPLC (Method 4) 98.0% (area under the curve), t _R = 12.14 minutes; ESI + APCI-MS m / z 516 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 2-nitrobenzyl) methylamine 8t (Example 22)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (2- nitrobenzyl) methylamine 8t, and to obtain an off-white solid (10% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.90 (d, J = 8.0Hz, 1H) , 7.73-7.66 (m, 2H), 7.52-7.48 (m, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.0, 7.6Hz, 1H), 6.62 (s, 1H), 4.00 (s , 3H), 3.94 (s, 2H), 3.93 (s, 3H), 3.77 (d, J = 12.8Hz, 2H), 2.73-2.67 (m, 2H), 2.39 (d, J = 6.0Hz, 2H) , 1.79 (d, J = 12.0 Hz, 2H), 1.58 (br s, 1H), 1.24-1.15 (m, 2H); HPLC (method 5) 96.9% (area under the curve), t _R = 6.65 minutes; ESI + APCI-MS m / z 536 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 3- (trifluoromethyl) benzyl) methylamine 8u (Example 23)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (3- (trifluoromethyl) benzyl) methylamine 8u, and in order to obtain an off-white solid (19% yield).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.5Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 7.71 (s, 1H), 7.66-7.52 ( m, 3H), 6.86 (s, 1H), 6.78 (d, J = 7.5Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 6.93 (s, 3H), 3.79-3.76 (m , 4H), 2.75-2.67 (m, 2H), 2.42-2.39 (m, 2H), 1.85-1.80 (m, 2H), 1.69-1.58 (m, 1H), 1.28-1.23 (m, 1H), 1.17 -1.15 (m, 1H); HPLC (method 3) 99.2% (area under the curve), t _R = 12.81 minutes; ESI + APCI-MS m / z 559 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of pyridin-3-ylmethyl) methylamine 8v (Example 24)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) - N - (pyridin-3-yl) methylamine 8v, and to obtain an off-white solid (15% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.52 (d, J = 1.6Hz, 1H), 8.43 (dd, J = 1.2, 4.4Hz, 1H), 8.26 (d, J = 7.6Hz, 1H) , 8.16 (s, 1H), 7.99 (s, 1H), 7.74 (d, J = 8.0Hz, 1H), 7.35-7.32 (m, 1H), 6.86 (s, 1H), 6.77 (dd, J = 2.0 , 7.6Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.77 (d, J = 12.8Hz, 2H), 3.72 (s, 2H), 2.74-2.68 (m, 2H), 2.41 (d, J = 6.4 Hz, 2H), 1.81 (d, J = 11.2 Hz, 2H), 1.62 (br s, 1H), 1.26-1.18 (m, 2H); HPLC (method 6) 97.6% (area under the curve), t _R = 11.17 minutes; ESI + APCI-MS m / z 492 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of pyridin-4-ylmethyl) methylamine 8w (Example 25)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyridin-4-ylmethyl) methylamine 8w and obtained as an off-white solid (19% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.50-8.47 (m, 2H), 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.35 ( d, J = 5.6Hz, 2H), 6.86 (s, 1H), 6.78 (dd, J = 2.0, 7.6Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H ), 3.78 (d, J = 12.4Hz, 2H), 3.73 (s, 2H), 2.74-2.66 (m, 2H), 2.40 (d, J = 6.4Hz, 2H), 1.82 (d, J = 11.2Hz , 2H), 1.63 (br s, 1H), 1.27-1.19 (m, 2H); HPLC (method 4) 91.8% (area under the curve), t _R = 11.09 minutes; ESI + APCI-MS m / z 492 [ M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of (3-fluoropyridin-4-yl) methyl) methylamine 8x (Example 26)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) piperidin-4-yl) -N -((3-fluoropyridin-4-yl) methyl) methylamine 8x and obtained as an off-white solid (16% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.46 (s, d, J = 1.6Hz 1H), 8.39 (dd, J = 0.8,4.8Hz, 1H), 8.26 (d, J = 7.6Hz, 1H ), 8.17 (s, 1H), 7.99 (s, 1H), 7.55 (t, J = 6.0 Hz, 1H), 6.86 (s, 1H), 6.77 (dd, J = 2.4, 7.6 Hz, 1H), 6.63 (d, J = 2.0Hz, 1H), 4.02 (s, 3H), 4.00 (s, 3H), 3.79 (s, 2H), 3.77 (d, J = 12.4Hz, 2H), 2.74-2.68 (m, 2H), 2.42 (d, J = 6.4Hz, 2H), 1.82 (d, J = 11.2Hz, 2H), 1.63 (br s, 1H), 1.28-1.18 (m, 2H); HPLC (Method 1) 95.7 % (Area under the curve), t _R = 11.73 minutes; ESI + APCI-MS m / z 510 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of (2-methoxypyridin-4-yl) methyl) methylamine 8y (Example 27)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) piperidin-4-yl) -N -((2-methoxypyridin-4-yl) methyl) methylamine 8y and obtained as an off-white solid (14% yield ).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.5Hz, 1H), 8.16 (s, 1H), 8.06 (d, J = 5.1Hz, 1H), 7.99 (s, 1H) , 6.95 (d, J = 5.4Hz, 1H), 6.86 (s, 1H), 6.83-6.78 (m, 2H), 6.63 (s, 1H), 4.0 (s, 3H), 3.93 (s, 3H), 3.82-3.76 (m, 6H), 3.68 (s, 2H), 2.75-2.67 (m, 3H), 2.37 (d, J = 6Hz, 2H), 1.82 (d, J = 11.7Hz, 2H), 1.28- 1.17 (m, 2H); HPLC (method 3) 96.9% (area under the curve), t _R = 11.94 minutes; ESI + APCI-MS m / z 522 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of thiazol-2-ylmethyl) methylamine 8z (Example 28)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) methylamine 8z and obtained as an off-white solid (13% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.69 (d, J = 3.2Hz, 1H) , 7.58 (d, J = 3.2Hz, 1H), 6.86 (s, 1H), 6.79 (dd, J = 2.0, 7.6Hz, 1H), 6.63 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.99 (s, 2H), 3.93 (s, 3H), 3.79 (d, J = 12.4Hz, 2H), 2.75-2.66 (m, 2H), 2.49 (d, J = 6.4Hz, 2H), 1.84 (d, J = 12.02 Hz, 2H), 1.63 (br s, 1H), 1.29-1.20 (m, 2H); HPLC (method 5) 97.0% (area under the curve), t _R = 6.45 minutes; ESI + APCI-MS m / z 498 [M + H] +.

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Pyrimidin-2-amine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) pyrimidin- Preparation of 2-amine) 8aa (Example 29)

(1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4- in DMF (2 mL) A solution of methyl) methylamine 6 (150 mg, 0.38 mmol) and 2-chloropyrimidine (2-chloropyrimidine) (66 mg, 0.58 mmol) was heated at 75 ° C for 16 hours. Water was added to the reaction mixture, and then a white precipitate formed. The solid was collected by vacuum filtration to obtain the crude product. With a combination of - flash chromatography analysis [silica gel; in MeOH: CH ₂ Cl _2: In (19) of 5% NH ₄ OH], purify the product. The product-containing fractions were combined and concentrated in vacuo to give N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Yl) piperidin-4-yl) methyl) pyrimidin-2-amine 8aa (20 mg, 11%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28-8.24 (m, 3H), 8.16 (s, 1H), 7.99 (s, 1H), 7.24 (t, J = 6.0Hz, 1H), 6.86 ( s, 1H), 6.79 (dd, J = 2.4,7.6Hz, 1H), 6.63 (d, J = 2.0Hz, 1H), 6.52 (t, J = 4.8Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.79 (d, J = 12.8Hz, 2H), 3.20 (t, J = 6.4Hz, 2H), 2.74-2.67 (m, 2H), 1.78 (d, J = 10.4Hz, 3H ), 1.30-1.23 (m, 2H); HPLC (method 1) 98.3% (area under the curve), t _R = 12.32 minutes; ESI + APCI-MS m / z 479 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N , N -Preparation of bis (pyridin-2-ylmethyl) methylamine 8ab (Example 30)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) piperidin-4-yl) -N, N-bis (pyridin-2-ylmethyl) methylamine 8ab and obtained as an off-white solid (15% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.48 (d, J = 4.0Hz, 2H), 8.26 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.99 (s, 1H) , 7.78 (t, J = 7.2Hz, 2H), 7.54 (d, J = 7.6Hz, 2H), 7.25 (t, J = 5.2Hz, 2H), 6.86 (s, 1H), 6.76 (d, J = 6.4Hz, 1H), 6.59 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.76-3.70 (m, 6H), 2.69 (t, J = 12.4Hz, 2H), 2.35 ( d, J = 6.0 Hz, 2H), 1.85 (d, J = 12.0 Hz, 3H), 1.10-1.02 (m, 2H); HPLC (method 3) 94.9% (area under the curve), t _R = 12.03 minutes; ESI + APCI-MS m / z 583 [M + H] ⁺ .

Preparation of ethyl 1- (2-aminopyridin-4-yl) piperidine-4-carboxylate (ethyl 1- (2-aminopyridin-4-yl) piperidine-4-carboxylate) 12

Of the N, N - diisopropylethylamine (N, N -diisopropylethylamine) 4- chloro-pyridine (25mL) -2- solution of amine 10 (2.00g, 15.6mmol), placed in a sealed tube, was added Ethyl piperidine-4-carboxylate 11 (3.67 g, 23.4 mmol). The tube was sealed and the reaction mixture was heated at 110 ° C for 16 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure, then the residue was separated between EtOAc and water (200 mL: 50 mL). The layers were separated, and the EtOAc layer was washed with brine (50 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated under reduced pressure to give the crude product. The product was triturated with hexane, filtered under reduced pressure and dried to give 1- (2-aminopyridin-4-yl) piperidine-4-carboxylic acid ethyl ester 12 (2.5 g, 85%) as an off-white solid, It was used in the next step without further purification.

ESI + APCI-MS m / z 250 [M + H] ⁺ .

1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4-carboxylic acid ethyl ester (ethyl 1- ( Preparation of 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidine-4-carboxylate) 13

At 75 ° C, 1- (2-aminopyridin-4-yl) piperidine-4-carboxylic acid 12 (2.5 g, 10.0 mmol) and 2-bromo-1- (5- A solution of chloro-2,4-dimethoxyphenyl) ethanone 4 (3.2 g, 11.0 mmol) was heated for 16 hours. The reaction mixture was cooled to room temperature, and then a white precipitate formed. The precipitate was collected by vacuum filtration and washed with hexane (200 mL). The crude product was suspended in water (200 mL) and saturated aqueous NaHCO ₃ solution (200 mL), and stirred at room temperature for 1 hour. The solid obtained was filtered under vacuum, washed with water and dried under vacuum to give ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) piperidin-4-yl) methyl) carbamic acid tert-butyl ester (tert -butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7 -yl) piperidin-4-yl) methyl) carbamate) 13 (1.2 g, 43.7%) as an off-white solid.

¹ H NMR (400MHz, CDCl ₃ ): δ 8.37 (s, 1H), 7.89-7.86 (m, 2H), 6.81 (s, 1H), 6.58 (s, 1H), 6.55 (dd, J = 2.4,7.6 Hz, 1H), 4.16 (q, J = 7.2Hz, 2H), 3.99 (s, 3H), 3.95 (s, 3H), 3.71-3.67 (m, 2H), 2.90-2.83 (m, 2H), 2.52 -2.46 (m, 1H), 2.06-2.03 (m, 2H), 1.92-1.83 (m, 2H), 1.27 (t, J = 7.2Hz, 3H); ESI + APCI MS m / z 444 [M + H ] ⁺ .

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4-carboxaldehyde (1- (2- (5 -chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4-carbaldehyde) 14

1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine in CH ₂ Cl ₂ (50 mL)- A solution of ethyl 4-carboxylate 13 (500 mg, 1.1 mmol) was cooled to -78 ° C, and DIBAL-H (1.1 mL, 1.6 mmol) was added thereto. The resulting mixture was stirred at -78 ° C for 1 hour. The reaction mixture was quenched with saturated aqueous NH ₄ Cl and extracted with CH ₂ Cl ₂ (2 × 50 mL). The combined organic layers were dried over anhydrous Na ₂ SO ₄ , filtered and concentrated under reduced pressure to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine -7-yl) piperidine-4-carbaldehyde 14 (300 mg, 76%) as an off-white solid, which was used in the next step without further purification.

ESI + APCI-MS m / z 400 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Cyclobutylamine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cyclobutanamine) 16a Preparation (Example 31)

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 in CH ₃ OH (5 mL) -A suspension of formaldehyde 14 (80 mg) and cyclobutanamine (21 mg, 0.30 mmol) was added to acetic acid (0.1 mL) and the resulting mixture was stirred for 2 hours. To this was added sodium cyanoborohydride (62 mg, 1.00 mmol), and the reaction mixture was stirred at room temperature for 15 minutes. The mixture reaction was diluted with aqueous NaHCO ₃ and extracted with _{CH 2 Cl 2 (2 × 20mL} ). The combined organic layers were dried over anhydrous Na ₂ SO _4, filtered and concentrated under reduced pressure to give the crude product. With a combination of - flash chromatography analysis [silica gel; in _{MeOH: CH 2 Cl 2 (1} : 9) NH in 5% ₄ OH], purification of the crude product. The product-containing fractions were combined and concentrated under reduced pressure to give N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Yl) piperidin-4-yl) methyl) cyclobutylamine 16a (17 mg, 19%) as an off-white solid.

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.76 (dd, J = 2.0, 7.6 Hz, 1H), 6.62 (d, J = 2.0 Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.77 (d, J = 12.4 Hz, 2H), 3.15 3.14 (m, 1H), 2.70 (t, J = 12.0Hz, 2H), 2.33 (d, J = 6.8Hz, 2H), 2.11-2.05 (m, 2H), 1.79 (d, J = 12.4Hz, 2H ), 1.68-1.50 (m, 5H), 1.24-1.16 (m, 2H); HPLC (method 3) 99.0% (area under the curve), t _R = 11.91 minutes; ESI + APCI MS m / z 455 [M + H] ⁺ .

2- (5-chloro-2,4-dimethoxyphenyl) -7- (4- (pyrrolidin-1-ylmethyl) piperidin-1-yl) imidazo [1,2-a] Preparation of pyridine (2- (5-chloro-2,4-dimethoxyphenyl) -7- (4- (pyrrolidin-1-ylmethyl) piperidin-1-yl) imidazo [1,2-a] pyridine) 16b

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare 2- (5-chloro-2,4-dimethoxyphenyl) -7- (4- (pyrrolidin-1-ylmethyl) piperidine-1- (Yl) imidazo [1,2-a] pyridine 16b and obtained as an off-white solid (16% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.77 (dd, J = 2.4,7.6Hz, 1H), 6.62 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.76 (d, J = 13.2Hz, 2H), 2.75- 2.69 (m, 2H), 2.41 (br s, 4H), 2.28 (d, J = 6.4Hz, 2H), 1.81 (d, J = 12.0Hz, 2H), 1.68 (br s, 5H), 1.23-1.16 (m, 2H); HPLC (method 5) 98.6% (area under the curve), t _R = 6.43 minutes; ESI + APCI MS m / z 455 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Cyclopentylamine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cyclopentanamine) 16c Preparation (Example 33)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) cyclopentylamine 16c and obtained as an off-white solid (12% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.03 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.86 (s, 1H), 6.96 (s, 1H), 6.67 (dd, J = 2.4,7.6Hz, 1H), 6.57 (d, J = 2.4Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.77 (d, J = 12.8Hz, 2H), 3.16-3.09 (m, 1H), 2.75-2.67 (m, 2H), 2.58 (d, J = 6.8Hz, 2H), 1.94-1.86 (m, 2H), 1.80 (d, J = 12.0Hz, 2H), 1.70- 1.62 (m, 3H), 1.54-1.48 (m, 2H), 1.40-1.23 (m, 4H); HPLC (method 3) 92.5% (area under the curve), t _R = 12.04 minutes; ESI + APCI MS m / z 469 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Tetrahydrofuran-3-amine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) tetrahydrofuran- 3-amine) 16d (Example 34)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) tetrahydrofuran-3-amine 16d and obtained as an off-white solid (yield 26%).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.0, 7.6 Hz, 1H), 6.63 (d, J = 2.0 Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.80-3.68 (m, 4H), 3.65-3.60 (m , 1H), 3.42-3.36 (m, 1H), 3.29-3.35 (m, 1H), 2.73-2.67 (m, 1H), 2.50-2.40 (m, 3H), 1.96-1.89 (m, 1H), 1.80 (d, J = 11.2Hz, 2H), 1.67-1.57 (m, 2H), 1.27-1.15 (m, 2H); HPLC (Method 3) 98.2% (area under the curve), t _R = 11.61 minutes; ESI + APCI MS m / z 471 [M + H] ⁺ .

2- (5-chloro-2,4-dimethoxyphenyl) -7- (4- (piperidin-1-ylmethyl) piperidin-1-yl) imidazo [1,2-a] Preparation of pyridine (2- (5-chloro-2,4-dimethoxyphenyl) -7- (4- (piperidin-1-ylmethyl) piperidin-1-yl) imidazo [1,2-a] pyridine) 16e (Example 35)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare 2- (5-chloro-2,4-dimethoxyphenyl) -7- (4- (piperidin-1-ylmethyl) piperidine-1- (Yl) imidazo [1,2-a] pyridine 16e and obtained as an off-white solid (17% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.4,7.6Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.77 (d, J = 12.4Hz, 2H), 2.75-2.67 (m, 2H ), 2.39-2.25 (m, 4H), 2.18-2.10 (m, 2H), 1.79-1.75 (m, 3H), 1.51 (br s, 4H), 1.39 (br s, 2H), 1.23-1.17 (m , 2H); HPLC (method 4) 96.3% (AUC), t _R = 6.50 minutes; ESI + APCI MS m / z 469 [m + H] +.

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Cyclohexylamine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cyclohexanamine) 16f Preparation (Example 36)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) cyclohexylamine 16f and obtained as an off-white solid (yield 20%).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.0, 7.6Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.4Hz, 2H), 2.74-2.67 (m, 2H ), 2.58 (d, J = 6.8Hz, 2H), 1.85-1.79 (m, 4H), 1.69-1.65 (m, 2H), 1.58-1.52 (m, 2H), 1.33-1.21 (m, 5H), 1.19-1.02 (m, 3H); HPLC (method 3) 92.3% (area under the curve), t _R = 12.24 minutes; ESI + APCI MS m / z 483 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Tetrahydro-2H-pyran-4-amine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4- Preparation of yl) methyl) tetrahydro-2H-pyran-4-amine) 16g (Example 37)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl 16 g of piperidin-4-yl) methyl) tetrahydro-2H-pyran-4-amine and obtained as an off-white solid (yield 25%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.03 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.86 (s, 1H), 6.69 (s, 1H), 6.67 (dd, J = 2.4, 7.6Hz, 1H), 6.57 (d, J = 2.0Hz, 1H), 3.92 (s, 3H), 3.87 (d, J = 4.0Hz, 2H), 3.85 (s, 3H), 3.75 (d , J = 12.8Hz, 2H), 3.35-3.28 (m, 2H), 2.74-2.60 (m, 3H), 2.49 (d, J = 6.8Hz, 2H), 1.81-1.76 (m, 4H), 1.66- 1.59 (m, 1H), 1.38-1.20 (m, 4H); HPLC (method 3) 98.4% (area under the curve), t _R = 11.66 minutes; ESI + APCI MS m / z 485 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of cycloheptylamine 16h (Example 38)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) cycloheptylamine for 16 h and obtained as an off-white solid (23% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 8.00 (s, 1H), 6.86 (s, 1H), 6.79 (dd, J = 2.4,7.6Hz, 1H), 6.66 (d, J = 1.6Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.81 (d, J = 12.4Hz, 2H), 2.88 ( br s, 1H), 2.75-2.67 (m, 4H), 1.96-1.80 (m, 4H), 1.75-1.60 (m, 3H), 1.56-1.32 (m, 8H), 1.30-1.22 (m, 2H) ; HPLC (Method 3) 98.9% (area under the curve), t _R = 12.48 minutes; ESI + APCI MS m / z 497 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 1-methylpiperidine-4-amine 16i (Example 39)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) -1-methylpiperidine-4-amine 16i and obtained as an off-white solid (yield 18%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.04 (d, J = 7.6Hz, 1H), 7.96 (s, 1H), 7.87 (s, 1H), 6.70-6.67 (m, 2H), 6.58 (d , J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.77 (d, J = 12.4Hz, 2H), 2.89-2.85 (m, 2H), 2.76-2.70 (m, 2H), 2.58 (d, J = 6.8Hz, 2H), 2.22 (s, 3H), 2.08-2.03 (m, 2H), 1.90 (d, J = 14.0Hz, 2H), 1.81 (d, J = 12.0 Hz, 2H), 1.68-1.64 (m, 1H), 1.47-1.37 (m, 2H), 1.33-1.23 (m, 2H), 1.19-1.17 (m, 1H); HPLC (Method 3) 97.7% (curve Lower area), t _R = 10.90 minutes; ESI + APCI MS m / z 498 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 1-Isopropylpiperidine-4-amine 16j (Example 40)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) -1-isopropylpiperidine-4-amine 16j and obtained as an off-white solid (34% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.0Hz, 7.6Hz, 1H), 6.58 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.8Hz, 2H), 2.73 -2.63 (m, 4H), 2.57-2.51 (m, 2H), 2.45 (d, J = 6.0Hz, 2H), 2.11-2.05 (m, 2H), 1.81-1.77 (m, 4H), 1.58-1.49 (m, 1H), 1.25-1.15 (m, 4H), 0.93 (d, J = 6.8Hz, 6H); HPLC (Method 3) 97.0% (area under the curve), t _R = 11.23 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of (1-methylpiperidin-4-yl) methyl) methylamine 16k (Example 41)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Piperidin-4-yl) -N -((1-methylpiperidin-4-yl) methyl) methylamine 16k and obtained as an off-white solid (yield 18%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.05 (d, J = 7.6Hz, 1H), 7.96 (s, 1H), 7.87 (s, 1H), 6.70-6.67 (m, 2H), 6.58 (d , J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.78 (d, J = 12.8Hz, 2H), 2.90 (d, J = 11.6Hz, 2H), 2.74 (t , J = 12.8Hz, 2H), 2.61 (t, J = 6.8Hz, 4H), 2.28 (s, 3H), 2.09 (t, J = 11.2Hz, 2H), 1.86-1.73 (m, 5H), 1.60 -1.54 (m, 1H), 1.35-1.17 (m, 4H); HPLC (Method 4) 94.6% (area under the curve), t _R = 6.28 minutes; ESI + APCI MS m / z 512 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 2- (1-methylpiperidin-4-yl) ethylamine 16l (Example 42)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) -2- (1-methylpiperidin-4-yl) ethylamine 16l, and obtained as an off-white solid (yield 11%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.03 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.86 (s, 1H), 6.69 (s, 1H), 6.66 (dd, J = 2.4, 7.6Hz, 1H), 6.57 (d, J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.75 (d, J = 12.4Hz, 2H), 2.79-2.69 (m, 4H), 2.58 (t, J = 7.6 Hz, 2H), 2.49 (d, J = 6.8 Hz, 2H), 2.16 (s, 3H), 1.93 (t, J = 10.0 Hz, 2H), 1.79 (d, J = 13.6Hz, 2H), 1.63 (d, J = 11.6Hz, 3H), 1.44-1.38 (m, 2H), 1.31-1.17 (m, 5H); HPLC (Method 4) 98.4% (curve Lower area), t _R = 6.29 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl ) -N ⁴ , N ⁴ -dimethylcyclohexane-1,4-diamine ( N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] pyridin-7-yl) piperidin-4-yl) methyl) -N ⁴ , N ⁴ -dimethylcyclohexane-1,4-diamine) 16m (Example 43)

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) formaldehyde Group) cyclobutylamine 16a to prepare N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- yl) piperidin-4-yl) methyl) - N ^4, N ⁴ - dimethylcyclohexane-1,4-diamine 16m, and to obtain an off-white solid (yield 11%).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.4,8.0Hz, 1H), 6.63 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.79 (d, J = 12.0Hz, 2H), 2.74- 2.60 (m, 4H), 2.16 (s, 6H), 2.04 (br s, 1H), 1.86-1.80 (m, 2H), 1.68-1.58 (m, 5H), 1.46-1.34 (m, 4H), 1.27 -1.19 (m, 3H); HPLC (method 1) 98.7% (area under the curve), t _R = 10.78 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

Option 3

((1- (2-amino-4-yl) pyrrolidin-3-yl) methyl) carbamic acid tert-butyl (tert -butyl ((1- (2 -aminopyridin-4-yl) pyrrolidin- Preparation of 3-yl) methyl) carbamate) 19

For a solution of 4-chloropyridine-2-amine 17 (500 mg, 3.90 mmol) in a mixture of n -butanol ( n- BuOH): N , N -diisopropylethylamine (10 mL / 5 mL), place it In a sealed tube, tert-butyl (pyrrolidin-3-ylmethyl) carbamate 18 (937 mg, 4.68 mmol) was added. The tube was sealed and the reaction mixture was heated at 120 ° C for 24 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure, then the residue was partitioned between EtOAc and saturated aqueous NaHCO _3: distinguishing between (100mL 50mL). The layers were separated, the EtOAc layer was washed with brine (50 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated under reduced pressure to give the crude product. The product was triturated with hexane, filtered under reduced pressure, and dried to give ((1- (2-aminopyridin-4-yl) pyrrolidin-3-yl) methyl) aminocarboxylic acid tert-butyl ester 19 (900 mg, 79%), as an off-white solid, which was used in the next step without further purification.

ESI + APCI-MS m / z 293 [M + H] ⁺ .

((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino tert-butyl (tert -butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) pyrrolidin-3-yl) methyl) carbamate) Preparation of 20

At 75 ° C, 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 4 (880 mg, 3.01 mmol) and ((1- ( A mixture of 2-aminopyridin-4-yl) pyrrolidin-3-yl) methyl) carbamic acid tert-butyl 19 (800 mg, 2.73 mmol) was heated for 16 hours. The reaction mixture was cooled to room temperature, and then a white precipitate formed. The precipitate was collected by vacuum filtration, washed with hexane (200 mL) and dried to give ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine -7-yl) pyrrolidin-3-yl) methyl) t-butyl carbamate 20 (600 mg, 45%) as an off-white solid.

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 12.99 (s, 1H), 8.49 (d, J = 7.6 Hz, 1H), 8.22 (s, 1H), 7.88 (s, 1H), 7.06 (t, J = 5.2Hz, 1H), 6.98 (s, 1H), 6.92 (d, J = 8.0Hz, 1H), 6.28 (s, 1H), 4.05 (s, 3H), 3.98 (s, 3H), 3.52- 3.44 (m, 3H), 3.18-3.16 (m, 1H), 3.03 (t, J = 6.8Hz, 2H), 2.51-2.49 (m, 1H), 2.12-2.08 (m, 1H), 1.87-1.72 ( m, 1H), 1.39 (s, 9H); HPLC (method 1) 95.82% (area under the curve), t _R = 14.25 minutes; ESI + APCI MS m / z 487 [M + H] ⁺ .

(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methylamine ((1- Preparation of (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) methanamine) 21a

((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrole in CH ₂ Cl ₂ (10 mL) A solution of alk-3-yl) methyl) carbamic acid tert-butyl ester 20 (600 mg, 1.23 mmol), a solution of HCl (4.0 M in 1,4-dioxane, 5 mL) was added and stirred at room temperature The reaction mixture was for 16 hours. The solid obtained in the reaction was collected by vacuum filtration and washed with CH ₂ Cl ₂ (100 mL) to obtain (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) pyrrolidin-3-yl) methylamine hydrochloride (400 mg, 84%) as an off-white solid.

¹ H NMR (300MHz, DMSO- d ₆ ): δ 13.55 (s, 1H), 8.53 (d, J = 7.5Hz, 1H), 8.25 (s, 1H), 8.13 (br s, 3H), 8.03 (s , 1H), 6.98 (s, 1H), 6.90 (d, J = 6.9Hz, 1H), 6.36 (s, 1H), 4.05 (s, 3H), 3.98 (s, 3H), 3.63-3.45 (m, 4H), 2.98-2.94 (m, 2H), 2.69-2.65 (m, 1H), 2.24-2.22 (m, 1H), 1.94-1.85 (m, 1H); HPLC (Method 1) 90.93% (area under the curve) ), T _R = 11.30 minutes; ESI + APCI MS m / z 387 [M + H] ⁺ .

Then, the solid 21a was suspended in water (15 mL), and the mixture was basified to pH 9 with a saturated sodium bicarbonate solution (15 mL), and then an off-white solid was precipitated. The solid produced in the mixture was collected by vacuum filtration, washed with water and dried to give (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) pyrrolidin-3-yl) methylamine 21b, which was used for further reactions without any purification.

ESI + APCI MS m / z 387 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2,2-dimethylpropan-1-amine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin- Preparation of 3-yl) methyl) -2,2-dimethylpropan-1-amine) 22a

For (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine in CH ₃ OH (10 mL)- A suspension of 3-yl) methylamine 21b (100 mg, 0.25 mmol) and pivalaldehyde (67 mg, 0.77 mmol), acetic acid (0.1 mL) was added, and the resulting mixture was stirred for 1 hour. Sodium cyanoborohydride (39 mg, 1.32 mmol) was added portionwise, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate (20 mL), and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated under reduced pressure to give the crude product. With a combination of - flash chromatography analysis [silica gel; in MeOH: CH ₂ Cl _2: In (19) of 5% NH ₄ OH], purify the product. The product-containing fractions were combined and concentrated in vacuo to give N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Pyrrolidin-3-yl) methyl) -2,2-dimethylprop-1-amine 22a (21 mg, 17%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2 Hz, 1H), 8.16 (s, 1H), 7.94 (s, 1H), 6.85 (s, 1H), 6.47 (dd, J = 2.0, 7.6Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.93 (s, 3H), 3.45-3.43 (m, 1H), 3.30-3.26 (m, 1H), 3.07 (dd, J = 6.8, 9.6Hz, 1H), 2.64-2.55 (m, 3H), 2.47-2.45 (m, 1H), 2.33-2.27 (m, 2H), 2.14-2.06 (m, 1H), 1.78 -1.69 (m, 1H), 0.89 (s, 9H); HPLC (method 5) 98.7% (area under the curve), t _R = 6.61 minutes; ESI + APCI-MS m / z 457 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of cyclopropylmethyl) methylamine 22b (Example 47)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (cyclopropylmethyl) methanamine 22b, and to obtain an off-white solid (16% yield).

¹ H NMR (300 MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2 Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 6.85 (s, 1H), 6.47 (d, J = 6.9Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.48-3.39 (m, 2H), 3.08-3.03 (m, 1H), 2.61-2.56 (m, 3H), 2.46-2.41 (m, 3H), 2.13-2.07 (m, 1H), 1.78-1.66 (m, 1H), 0.95-0.85 (m, 1H), 0.46-0.35 (m, 2H) 0.14-0.08 (m, 2H); HPLC (Method 1) 97.46% (area under the curve), t _R = 11.74 minutes; ESI + APCI MS m / z 441 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of cyclopentylmethyl) methylamine 22c (Example 48)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (cyclopentylmethyl) methanamine 22c, and to obtain an off-white solid (18% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.95 (s, 1H), 6.85 (s, 1H), 6.47 (dd, J = 2,7.2Hz, 1H), 6.20 (d, J = 2Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.49-3.46 (m, 1H), 3.41-3.38 (m, 2H), 3.12-3.08 (m, 1H), 2.82 (br s, 1H), 2.69-2.60 (m, 1H), 2.59-2.54 (m, 2H), 2.14-2.04 (m, 2H), 1.80-1.73 (m, 3H), 1.60-1.48 (m, 5H), 1.23-1.18 (m, 2H); HPLC (method 5) 94.60% (area under the curve), t _R = 6.63 minutes; ESI + APCI MS m / z 469 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde yl) amino) methyl) pyrrolidine-1-carboxylate (tert -butyl 3 - ((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ) pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylate) 22d (Example 49)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 22a in the same manner to prepare 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazolo [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 22d and obtained as an off-white solid (yield 34 %).

¹ H NMR (300 MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2 Hz, 1H), 8.16 (s, 1H), 7.93 (s, 1H), 6.85 (s, 1H), 6.46 (d, J = 7.2Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.47-3.42 (m, 3H), 3.31-3.25 (m, 2H), 3.20-3.17 (m, 1H), 3.08-3.02 (m, 1H), 2.95-2.90 (m, 1H), 2.61-2.51 (m, 3H), 2.50-2.41 (m, 2H), 2.31-2.27 (m, 1H) , 2.12-2.08 (m, 1H), 1.91 (br s, 1H), 1.75-1.66 (m, 1H), 1.58-1.49 (m, 1H), 1.39 (s, 9H); HPLC (Method 5) 99.76% (Area under the curve), t _R = 6.54 minutes; ESI + APCI MS m / z 570 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of pyrrolidin-3-ylmethyl) methylamine 22e (Example 50)

3-((((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) in 2,2,2-trifluoroethanol (3.0 mL) at 0 ° C [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl 22d solution (100.0 mg), trimethyl added Silyl chloride (0.1 mL). The reaction mixture was stirred at 0 ° C for 30 minutes. The reaction mixture was evaporated to dryness and washed with hexane to give 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) Pyrrolidin-3-yl) -N- (pyrrolidin-3-ylmethyl) methylamine 22e pure hydrochloride (25 mg, 30%) as an off-white solid.

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 13.83 (br s, 1H), 9.52-9.43 (m, 4H), 8.53 (d, J = 7.6 Hz, 1H), 8.24 (s, 1H), 8.10 (s, 1H), 6.95 (s, 1H), 6.89 (d, J = 6.4Hz, 1H), 6.39 (s, J = 1.6Hz, 1H), 4.05 (s, 3H), 3.98 (s, 3H) , 3.76-3.69 (m, 1H), 3.65-3.53 (m, 1H), 3.48-3.36 (m, 3H), 3.29-3.21 (m, 1H), 3.19-3.01 (m, 6H), 2.92-2.85 ( m, 1H), 2.82-2.74 (m, 1H), 2.31-2.24 (m, 1H), 2.19-2.11 (m, 1H), 1.98-1.89 (m, 1H), 1.82-1.70 (m, 1H); HPLC (method 5) 98.12% (AUC), t _R = 6.10 minutes; ESI + APCI MS m / z 470 [m + H] +.

4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl Of amino) amino) methyl) piperidine-1-carboxylic acid tert-butyl 22f (Example 51)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 22a, 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 22f, obtained as an off-white solid (yield 40) %).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.25 (d, J = 7.5Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 6.85 (s, 1H), 6.46 (d, J = 7.8Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.95-3.89 (m, 6H), 3.47-3.36 (m, 2H), 3.08-3.03 (m, 1H), 2.68 -2.51 (m, 6H), 2.17-2.08 (m, 1H), 1.78-1.56 (m, 5H), 1.38 (s, 9H), 1.02-0.91 (m, 2H); HPLC (Method 1) 99.1% ( Area under the curve), t _R = 12.41 minutes; ESI + APCI MS m / z 584 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of piperidin-4-ylmethyl) methylamine 22g (Example 52)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(Pyrrolidin-3-ylmethyl) methylamine 22e to prepare 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) pyrrolidin-3-yl) - N - (piperidin-4-yl) methylamine 22g, and to obtain an off-white solid (30% yield).

¹ H NMR (300 MHz, DMSO- d ₆ ): δ 13.82 (br s, 1H), 9.40-9.28 (m, 2H), 9.06-8.82 (m, 2H), 8.53 (d, J = 7.5 Hz, 1H) , 8.25 (s, 1H), 8.11 (s, 1H), 6.97 (s, 1H), 6.90 (d, J = 7.2Hz, 1H), 6.40 (s, 1H), 4.05 (s, 3H), 3.98 ( s, 3H), 3.76-3.68 (m, 1H), 3.64-3.56 (m, 1H), 3.49-3.38 (m, 2H), 3.30-3.22 (m, 2H), 3.12-3.02 (m, 2H), 2.94-2.78 (m, 5H), 2.30-2.20 (m, 1H), 2.19-1.85 (m, 4H), 1.51-1.37 (m, 2H); HPLC (Method 1) 95.52% (area under the curve), t _R = 10.99 minutes; ESI + APCI MS m / z 484 [M + H] ⁺ .

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Preparation of methylamine 22h (Example 53)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl)) Imidazolo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methylamine was obtained for 22 h and was obtained as an off-white solid (yield 20%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 7.37-7.30 (m, 4H), 7.24- 7.21 (m, 1H), 6.85 (s, 1H), 6.46 (dd, J = 2.4,7.6Hz, 1H), 6.18 (d, J = 1.6Hz, 1H), 3.99 (s, 3H), 3.92 (s , 3H), 3.75 (s, 2H), 3.48-3.44 (m, 1H), 3.30-3.25 (m, 2H), 3.09-3.05 (m, 1H), 2.63-2.53 (m, 3H), 2.15-2.05 (m, 1H), 1.77-1.70 (m, 1H); HPLC (method 4) 98.67% (area under the curve), t _R = 12.19 minutes; ESI + APCI MS m / z 477 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 2-fluorobenzyl) methylamine 22i (Example 54)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (2- fluorobenzyl) methylamine 22i, and to obtain an off-white solid (19% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6 Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 7.50-7.47 (m, 1H), 7.29- 7.25 (m, 1H), 7.19-7.12 (m, 2H), 6.85 (s, 1H), 6.46 (dd, J = 2.4, 7.6Hz, 1H), 6.18 (d, J = 2Hz, 1H), 3.99 ( s, 3H), 3.92 (s, 3H), 3.77 (s, 2H), 3.48-3.44 (m, 1H), 3.37-3.27 (m, 2H), 3.09-3.04 (m, 1H), 2.60-2.53 ( m, 3H), 2.15-2.05 (m, 1H), 1.76-1.69 (m, 1H); HPLC (method 1) 91.20% (area under the curve), t _R = 11.94 minutes; ESI + APCI MS m / z 495 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 3-fluorobenzyl) methylamine 22j (Example 55)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) pyrrolidin-3-yl) -N- (3-fluorobenzyl) methylamine 22j, and obtained as an off-white solid (yield 20%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 7.38-7.32 (m, 1H), 7.21- 7.18 (m, 2H), 7.07-7.02 (m, 1H), 6.85 (s, 1H), 6.47 (dd, J = 2.4, 7.6Hz, 1H), 6.18 (d, J = 1.6Hz, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.77 (s, 2H), 3.49-3.44 (m, 1H), 3.38-3.28 (m, 2H), 3.09-3.05 (m, 1H), 2.61-2.53 (m, 3H), 2.16-2.08 (m, 1H), 1.76-1.69 (m, 1H); HPLC (Method 4) 97.66% (area under the curve), t _R = 11.97 minutes; ESI + APCI MS m / z 495 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 4-fluorobenzyl) methylamine 22k (Example 56)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (cyclopropylmethyl) methanamine 22k, and to obtain an off-white solid (14% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.25 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 7.40-7.36 (m, 2H), 7.15- 7.10 (m, 2H), 6.85 (s, 1H), 6.46 (dd, J = 2.4, 7.6Hz, 1H), 6.18 (d, J = 1.6Hz, 1H), 3.99 (s, 3H), 3.92 (s , 3H), 3.71 (s, 2H), 3.48-3.43 (m, 1H), 3.38-3.25 (m, 2H), 3.08-3.04 (m, 1H), 2.60-2.44 (m, 3H), 2.14-2.08 (m, 1H), 1.75-1.68 (m, 1H); HPLC (method 1) 99.41% (area under the curve), t _R = 12.02 minutes; ESI + APCI MS m / z 495 [M + H] ⁺ .

4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl (Amino) amino) methyl) -N , N -dimethylaniline 22l (Example 57)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 22a, 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N , N -dimethylaniline 22l, obtained as an off-white solid (yield 8%) ).

¹ H NMR (400MHz, DMSO- d ₆ ) δ: 8.29 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.95 (s, 1H), 7.26 (d, J = 8.4Hz, 2H) , 6.86 (s, 1H), 6.73 (d, J = 8.8Hz, 2H), 6.47 (dd, J = 2.4, 7.6Hz, 1H), 6.20 (s, 1H), 4.10 (s, 3H), 4.0 ( s, 3H), 3.93 (br s, 2H), 3.49-3.47 (m, 1H), 3.43-3.38 (m, 1H), 3.12-3.08 (m, 1H), 2.99 (s, 6H), 2.94-2.85 (m, 2H), 2.62-2.56 (m, 2H), 2.18-2.09 (m, 1H), 1.84-1.75 (m, 1H); HPLC (method 5) 97.2% (area under the curve), t _R = 13.72 Minutes; ESI + APCI MS m / z 520 [M + H] ⁺ .

4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl (Methyl) amino) methyl) phenol 22m (Example 58)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylprop-1-amine 22a, 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) phenol 22 m, and obtained as an off-white solid (yield 15%).

¹ H NMR (400 MHz, DMSO- d ₆ ) δ: 9.34 (br s, 1H), 8.27 (d, J = 7.6 Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 7.18 (d , J = 8.4Hz, 2H), 6.85 (s, 1H), 6.72 (d, J = 8.4Hz, 2H), 6.47 (dd, J = 2.0, 7.6Hz, 1H), 6.18 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.73 (br s, 2H), 3.49-3.45 (m, 1H), 3.28-3.26 (m, 2H), 3.08-3.05 (m, 1H), 2.67 ( br s, 2H), 2.14-2.10 (m, 1H), 1.78-1.65 (m, 1H); HPLC (method 5) 97.2% (area under the curve), t _R = 13.72 minutes; ESI + APCI MS m / z 493 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 2-nitrobenzyl) methylamine 22n (Example 59)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (2- nitrobenzyl) methylamine 22n, and to obtain an off-white solid (17% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.6Hz, 1H), 8.12 (s, 1H), 7.97 (s, 1H), 7.93 (d, J = 7.6Hz, 1H) , 7.73-7.67 (m, 2H), 7.53-7.50 (m, 2H), 6.87 (s, 1H), 6.51 (dd, J = 2.4, 7.6Hz, 1H), 6.19 (s, 1H), 4.03 (m , 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.37-3.42 (m, 2H), 3.29-3.27 (m, 1H), 3.07-3.05 (m, 1H), 2.60-2.55 (m , 3H), 2.46-2.41 (m, 2H), 2.11-2.08 (m, 1H), 1.74-1.69 (m, 1H); HPLC (Method 1) 97.1% (area under the curve), t _R = 11.86 minutes; ESI + APCI-MS m / z 522 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 3- (trifluoromethyl) benzyl) methylamine 22o (Example 60)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (3- (trifluoromethyl) benzyl) methylamine 22o, and to obtain an off-white solid (23% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.94 (s, 1H), 7.73 (s, 1H), 7.68-7.66 ( m, 1H), 7.60-7.53 (m, 2H), 6.85 (s, 1H), 6.46 (dd, J = 2, 7.2 Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.93 (s, 3H), 3.83 (s, 2H), 3.49-3.44 (m, 1H), 3.38-3.36 (m, 1H), 3.30-3.26 (m, 1H), 3.09 (d, J = 6.8,9.6Hz , 1H), 2.58-2.55 (m, 3H), 2.15-2.08 (m, 1H), 1.78-1.69 (m, 1H); HPLC (method 3) 97.4% (area under the curve), t _R = 12.69 minutes; ESI + APCI-MS m / z 545 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 4- (trifluoromethyl) benzyl) methylamine 22p (Example 61)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (4- (trifluoromethyl) benzyl) methylamine 22p, and to obtain an off-white solid (13% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.95 (s, 1H), 7.68 (d, J = 8.0Hz, 2H) , 7.59 (d, J = 8.0Hz, 2H), 6.18 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.84 (s, 2H), 3.47 (dd, J = 7.6, 10Hz , 1H), 3.37-3.36 (m, 1H), 3.30-3.29 (m, 2H), 3.10-3.06 (m, 1H), 2.59-2.56 (m, 2H), 2.15-2.08 (m, 1H), 1.78 -1.69 (m, 1H); HPLC (method 5) 99.8% (area under the curve), t _R = 6.81 minutes; ESI + APCI-MS m / z 545 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- ( Preparation of 4-methylbenzyl) methylamine 22q (Example 62)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) pyrrolidin-3-yl) -N- (4-methylbenzyl) methylamine 22q, and obtained as an off-white solid (yield 26%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.25 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 7.23 (d, J = 8.0Hz, 2H) , 7.11 (d, J = 8.0 Hz, 2H), 6.85 (s, 1H), 6.46 (dd, J = 2.0, 7.6 Hz, 1H), 6.17 (s, 1H), 3.99 (s, 3H), 3.92 ( s, 3H), 3.68 (s, 2H), 3.47-3.43 (m, 1H), 3.30-3.25 (m, 1H), 3.07-3.03 (m, 1H), 2.51-2.47 (m, 4H), 2.27 ( s, 3H), 2.13-2.07 (m, 1H), 1.76-1.67 (m, 1H); HPLC (method 5) 99.3% (area under the curve), t _R = 6.70 minutes; ESI + APCI-MS m / z 491 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- ( Preparation of 2-chlorobenzyl) methylamine 22r (Example 63)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) pyrrolidin-3-yl) -N- (2-chlorobenzyl) methylamine 22r, and obtained as an off-white solid (yield 25%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.14 (s, 1H), 7.95 (s, 1H), 7.57 (dd, J = 1.2, 7.2Hz, 1H), 7.42 (dd, J = 1.2, 8.0 Hz, 1H), 7.35-7.25 (m, 2H), 6.85 (s, 1H), 6.49 (dd, J = 2.4, 7.6 Hz, 1H), 6.19 (s , 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.83 (s, 2H), 3.50-3.46 (m, 1H), 3.39-3.35 (m, 1H), 3.12-3.08 (m, 1H ), 2.63-2.60 (m, 2H), 2.51-2.47 (m, 2H), 2.17-2.08 (m, 1H), 1.79-1.74 (m, 1H); HPLC (method 5) 95.2% (area under the curve) , T _R = 6.66 minutes; ESI + APCI-MS m / z 511 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 4-chlorobenzyl) methylamine 22s (Example 64)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (4- chlorobenzyl) methylamine 22s, and to obtain an off-white solid (25% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 7.39-7.35 (m, 4H), 6.85 ( s, 1H), 6.47 (dd, J = 2.0, 7.6 Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.72 (s, 2H), 3.48-3.43 (m, 1H), 3.29-3.25 (m, 1H), 3.08-3.04 (m, 1H), 2.51-2.47 (m, 4H), 2.12-2.08 (m, 1H), 1.77-1.68 (m, 1H) ; HPLC (Method 5) 99.1% (area under the curve), t _R = 6.70 minutes; ESI + APCI-MS m / z 511 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of pyridin-3-ylmethyl) methylamine 22t (Example 65)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (pyridin-3-yl) methylamine 22t, and to obtain an off-white solid (16% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.54 (s, 1H), 8.43 (dd, J = 1.6, 4.6 Hz, 1H), 8.25 (d, J = 7.6 Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 7.78-7.75 (m, 1H), 7.36-7.32 (m, 1H), 6.85 (s, 1H), 6.46 (dd, J = 2.4, 7.2Hz, 1H), 6.18 (d, J = 2Hz, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.74 (s, 2H), 3.48-3.44 (m, 1H), 3.38-3.32 (m, 1H), 3.32 -3.28 (m, 1H), 3.08-3.04 (m, 1H), 2.60-2.44 (m, 3H), 2.15-2.09 (m, 1H), 1.75-1.69 (m, 1H); HPLC (Method 5) 96.39 % (Area under the curve), t _R = 6.14 minutes; ESI + APCI MS m / z 478 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of pyridin-4-ylmethyl) methylamine 22u (Example 66)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (pyridin-4-yl) methylamine 22u, and to obtain an off-white solid (13% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.48 (dd, J = 1.6, 4.6 Hz, 2H), 8.26 (d, J = 7.6 Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 7.37 (d, J = 2.0Hz, 2H), 6.85 (s, 1H), 6.47 (dd, J = 2.0, 7.6Hz, 1H), 6.18 (d, J = 1.2Hz, 1H), 3.99 ( s, 3H), 3.92 (s, 3H), 3.75 (s, 2H), 3.49-3.42 (m, 1H), 3.32-3.26 (m, 1H), 3.10-3.06 (m, 1H), 2.59-2.47 ( m, 2H), 2.15-2.09 (m, 1H), 1.78-1.68 (m, 1H); HPLC (method 1) 91.29% (area under the curve), t _R = 11.09 minutes; ESI + APCI MS m / z 478 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (3-fluoropyridin-4-yl) methyl) methylamine 22v (Example 67)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) pyrrolidin-3-yl) -N -((3-fluoropyridin-4-yl) methyl) methylamine 22v, and obtained as an off-white solid (yield 13%).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.47 (s, 1H), 8.39 (d, J = 4.8Hz, 1H), 8.26 (d, J = 7.5Hz, 1H), 8.15 (s, 1H) , 7.94 (s, 1H), 7.59-7.55 (m, 1H), 6.85 (s, 1H), 6.47 (d, J = 6.3Hz, 1H), 6.19 (s, 1H), 4.00 (s, 3H), 3.92 (s, 3H), 3.82 (s, 2H), 3.49-3.39 (m, 3H), 3.11-3.07 (m, 1H), 2.59-2.47 (m, 3H), 2.15-2.09 (m, 1H), 1.79-1.69 (m, 1H); HPLC (method 1) 99.90% (area under the curve), t _R = 11.59 minutes; ESI + APCI MS m / z 496 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (2-fluoropyridin-4-yl) methyl) methylamine 22w (Example 1)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) pyrrolidin-3-yl) -N -((2-fluoropyridin-4-yl) methyl) methylamine 22w, and obtained as an off-white solid (yield 17%).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.5Hz, 1H), 8.16-8.12 (m, 2H), 7.94 (s, 1H), 7.35 (br s, 1H), 7.15 (s, 1H), 6.85 (s, 1H), 6.48 (d, J = 7.2Hz, 1H), 6.19 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.81 (s, 2H), 3.50-3.42 (m, 3H), 3.11-3.07 (m, 1H), 2.59-2.47 (m, 3H), 2.14-2.08 (m, 1H), 1.78-1.68 (m, 1H); HPLC ( Method 4) 98.66% (area under the curve), t _R = 11.80 minutes; ESI + APCI MS m / z 496 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N , N -Preparation of bis (pyridin-2-ylmethyl) methylamine 22x (Example 2)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2,2-dimethylpropan-1-amine 22a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) pyrrolidin-3-yl) -N , N -bis (pyridin-2-ylmethyl) methylamine 22x, and a yield (10%) was obtained as an off-white solid.

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.47 (dd, J = 0.8, 4.8 Hz, 2H), 8.25 (d, J = 7.2 Hz, 1H), 8.16 (s, 1H), 7.94 (s, 1H), 7.77-7.73 (m, 2H), 7.57 (d, J = 7.6Hz, 2H), 7.24-7.21 (m, 2H), 6.85 (s, 1H), 6.43 (dd, J = 2.0, 7.6Hz , 1H), 6.14 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (q, J = 14.4Hz, 4H), 3.44-3.39 (m, 1H), 3.24-3.17 ( m, 2H), 3.03-2.99 (m, 1H), 2.69-2.63 (m, 2H), 2.50-2.48 (m, 1H), 2.08-2.04 (m, 1H), 1.68-1.62 (m, 1H); HPLC (Method 1) 96.8% (area under the curve), t _R = 11.89 minutes; ESI + APCI MS m / z 569 [M + H] ⁺ .

Preparation of methyl 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylate 23

For a solution of 4-chloropyridine-2-amine (0.48 g, 3.75 mmol) in N , N -diisopropylethylamine (10 mL), place it in a sealed tube and add pyrrolidine-3-carboxylic acid forma Methyl pyrrolidine-3-carboxylate (0.93 g, 5.65 mmol). The tube was sealed and the reaction mixture was heated at 120 ° C for 16 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure, and the residue was partitioned between EtOAc and saturated aqueous NaHCO _3: distinguishing between (300mL 100mL). The layers were separated, the EtOAc layer was washed with brine (10 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated under reduced pressure to give the crude product. The product was triturated with hexane, filtered under reduced pressure and dried to give 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylic acid methyl ester 23 (700 mg, crude) as an off-white A solid, which was used directly in the next step without further purification.

ESI + APCI-MS m / z 222 [M + H] ⁺ .

1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid methyl ester (methyl 1- ( Preparation of 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidine-3-carboxylate) 24

At 75 ° C, methyl 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylate 23 (0.50 g, 2.262 mmol) and 2-bromo-1- ( A mixture of 5-chloro-2,4-dimethoxyphenyl) ethanone 4 (0.726 g, 2.48 mmol) was heated for 16 hours. The reaction mixture was cooled to room temperature, and then a white precipitate formed. The precipitate was collected by vacuum filtration, washed with hexane (20 mL) and dried to give the hydrobromide salt, which was treated with an aqueous solution of NaHCO ₃ (5.0 mL) to give 1- (2- (5-chloro-2, The free base (0.2 g, 47%) of 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid methyl ester 24 was an off-white solid.

¹ H NMR (400MHz, CDCl ₃ ): δ 8.31 (s, 1H), 7.80 (d, J = 7.2Hz, 1H), 7.74 (s, 1H), 6.50 (s, 1H), 6.41 (s, 1H) , 6.28 (dd, J = 2.0, 7.2 Hz, 1H), 3.92 (s, 3H), 3.88 (s, 3H), 3.68 (s, 3H), 3.56 (d, J = 7.2Hz, 2H), 3.44- 3.40 (m, 1H), 3.37-3.31 (m, 1H), 3.22-3.15 (m, 1H), 2.29-2.24 (m, 2H). ESI + APCI-MS m / z 416 [M + H] ⁺ .

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid (1- (2- ( Preparation of 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid) 25

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 in THF, CH ₃ OH, and water (20 mL / 10 mL / 5 mL) -Methyl) pyrrolidine-3-carboxylic acid methyl ester 24 (1.0 g, 2.4 mmol) was added to LiOH‧H ₂ O (0.40 g, 9.6 mmol), and the resulting mixture was stirred at ambient temperature for 5 hours. The reaction mixture was evaporated and diluted with water, and extracted with ethylacetate (2 x 10 mL). The aqueous layer was adjusted to a pH of 3 to 4 with a 10% KHSO ₄ solution to obtain a precipitate. The precipitate was filtered, washed and dried to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3 -Carboxylic acid 25 (750 mg, 78%) as an off-white solid.

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.5Hz, 1H), 8.16 (s, 1H), 7.96 (s, 1H), 6.85 (s, 1H), 6.51 (d, J = 6.6Hz, 1H), 6.24 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.57-3.46 (m, 2H), 3.37-3.33 (m, 2H), 3.25-3.18 (m, 1H), 2.27-2.17 (m, 2H); ESI + APCI MS m / z 402 [M + H] ⁺ .

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) -N -methoxy- N -methylpyrrolidine- 3-methylpyramine (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) -N -methoxy- N -methylpyrrolidine-3-carboxamide) 26 Preparation

For 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- in DMF (2.0 mL) carboxylic acid 25 (0.2g, 0.498mmol), N , O - dimethylhydroxylamine hydrochloride (N, O -Dimethylhydroxylamine hydrochloride) ( 72mg, 0.747mmol) and N, N - diisopropylethylamine (N, N- diisopropylethyl amine) (256mg, 1.99) solution, add EDC. HCl (190 mg, 0.996 mmol) and HOBt (152 mg, 0.996 mmol), and the resulting mixture was stirred at ambient temperature for 15 hours. The reaction mixture was diluted with water to give a precipitate. The precipitate was extracted with ethyl acetate (2 × 10 mL). The organic layer was dried over anhydrous Na ₂ SO ₄ and concentrated to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) -N -methoxy- N -methylpyrrolidine-3-carboxamide 26 (200 mg, raw). The crude compound was used as such in the next step.

¹ H NMR (300 MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.95 (s, 1H), 6.85 (s, 1H), 6.51 (d, J = 7.5Hz, 1H), 6.23 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.72 (s, 3H), 3.59-3.55 (m, 2H), 3.42-3.37 (m 3H), 3.15 (s, 3H), 2.26-2.08 (m, 2H); ESI + APCI MS m / z 445 [M + H] ⁺ .

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxaldehyde (1- (2- (5 -chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidine-3-carbaldehyde) 27

Add 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) -N -methoxy in THF (500 mL) -A solution of N -methylpyrrolidine-3-carboxamide 26 (1.0 g, 2.25 mmol) was cooled to -78 ° C. To the resulting reaction mixture was added 2.0M LAH (3.37 mL, 6.75 mmol) in THF at -78 ° C. The resulting reaction mixture was stirred for an additional hour at -78 ° C. With aqueous NH ₄ Cl the reaction mixture was quenched and extracted with ethyl acetate (2 × 50mL). The organic layer was dried over anhydrous Na ₂ SO ₄ and concentrated to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidine-3-carbaldehyde 27 (800 mg, raw). The crude compound was used as such in the next step.

ESI + APCI MS m / z 386 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -3,3-dimethylbut-1-amine ( N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin- Preparation of 3-yl) methyl) -3,3-dimethylbutan-1-amine) 28a

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3 in CH ₃ OH (5 mL) -A suspension of formaldehyde 27 (100 mg, 0.25 mmol) and 3,3-dimethylbutan-1-amine (34 mg, 0.38 mmol) was added to acetic acid (0.05 mL), and The resulting mixture was stirred for 2 hours. Sodium cyanoborohydride (48 mg, 0.55 mmol) was added, and the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was diluted with aqueous sodium bicarbonate solution and extracted with CH ₂ Cl ₂ (2 × 10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure, and the residue was purified by combi-flash companion (silica gel, NH ₄ OH / CH ₃ OH / CH ₂ Cl ₂ ) To give N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde ) -3,3-dimethylbut-1-amine 28a (25 mg, 20%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ) δ: 8.25 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.93 (s, 1H), 6.82 (s, 1H), 6.47 (dd, J = 2.4, 7.6Hz, 1H), 6.10 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.38-3.34 (m, 1H), 3.39-3.23 (m, 4H), 3.06 -3.02 (m, 1H), 2.60-2.52 (m, 2H), 2.46-2.37 (m, 1H), 2.12-2.05 (m, 1H), 1.76-1.67 (m, 1H), 1.36-1.32 (m, 2H), 0.88 (s, 9H); HPLC (method 3) 90.5% (area under the curve), t _R = 12.5 minutes; ESI + APCI MS m / z 471 [M + H] ⁺ .

N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of -2-methoxyethylamine 28b (Example 32)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -3,3-dimethylbut-1-amine 28a by the same method to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) -2-methoxyethylamine 28b and obtained as an off-white solid (21% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ) δ: 8.26 (d, J = 7.2 Hz, 1H), 8.15 (s, 1H), 7.95 (s, 1H), 6.85 (s, 1H), 6.47 (dd, J = 2.0, 7.2Hz, 1H), 6.10 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.46-3.36 (m, 4H), 3.32 (br s, 3H), 3.06- 3.02 (m, 1H), 2.96 (t, J = 5.6Hz, 2H), 2.62 (t, J = 7.2Hz, 2H), 2.57 (t, J = 7.6Hz, 2H), 2.17-2.06 (m, 1H ), 1.85-1.67 (m, 1H); HPLC (Method 3) 96.7% (area under the curve), t _R = 11.61 minutes; ESI + APCI MS m / z 445 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of cyclobutylamine 28c (Example 44)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -3,3-dimethylbut-1-amine 28a by the same method to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) cyclobutylamine 28c and obtained as an off-white solid (yield 19%).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.5Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 6.85 (s, 1H), 6.48 (d, J = 7.2Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.932 (s, 3H), 3.46-3.40 (m, 2H), 3.33-3.27 (m, 1H), 3.16 (br s, 1H), 3.06-3.01 (m, 1H), 2.41-2.32 (m, 2H), 2.10-2.08 (m, 3H), 1.08-1.49 (m, 6H); HPLC (Method 4) 96.9% (curve Lower area), t _R = 6.50 minutes; ESI + APCI MS m / z 441 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) 1-methylpiperidine-4-amine 28d (Example 45)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -3,3-dimethylbut-1-amine 28a by the same method to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) -1-methylpiperidin-4-amine 28d and obtained as an off-white solid (16% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ) δ: 8.26 (d, J = 7.2 Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 6.85 (s, 1H), 6.47 (dd, J = 2.4, 7.6Hz, 1H), 6.18 (d, J = 1.6Hz, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.47-3.43 (m, 1H), 3.42-3.27 (m , 2H), 3.07-3.03 (m, 1H), 2.71-2.66 (m, 2H), 2.62-2.55 (m, 2H), 2.45-2.36 (m, 2H), 2.13-2.06 (m, 4H), 1.90 -1.85 (m, 2H), 1.79-1.68 (m, 3H), 1.29-1.23 (m, 2H); HPLC (Method 3) 99.3% (area under the curve), t _R = 11.03 minutes; ESI + APCI MS m / z 484 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-methylpiperidin-4-yl) methyl) methylamine 28e (Example 46)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -3,3-dimethylbut-1-amine 28a by the same method to prepare 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridine-7-yl) pyrrolidin-3-yl) -N -((1-methylpiperidin-4-yl) methyl) methylamine 28e and obtained as an off-white solid (yield 15% ).

¹ H NMR (400 MHz, DMSO- d ₆ ) δ: 8.26 (d, J = 7.6 Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 6.85 (s, 1H), 6.46 (dd, J = 2.4, 7.6Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.46-3.42 (m, 1H), 3.31-3.28 (m, 2H), 3.07 -3.03 (m, 1H), 2.73 (d, J = 2.4, 11.2Hz, 2H), 2.55-2.51 (m, 2H), 2.40 (d, J = 6.8Hz, 3H), 2.13-2.07 (m, 4H ), 1.82-1.77 (m, 2H), 1.72-1.65 (m, 3H), 1.35-1.30 (m, 1H), 1.64-1.09 (m, 2H); HPLC (method 3) 95.7% (area under the curve) , T _R = 11.07 minutes; ESI + APCI MS m / z 498 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of aniline 28f (Example 68)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -3,3-dimethylbut-1-amine 28a by the same method to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) aniline 28f and obtained as an off-white solid (yield 19%).

¹ H NMR (400MHz, DMSO- d ₆ ) δ: 8.27 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.95 (s, 1H), 7.07 (t, J = 8.4Hz, 2H) , 6.85 (s, 1H), 6.60 (d, J = 7.6Hz, 2H), 6.59-6.49 (m, 2H), 6.20 (s, 1H), 4.01 (s, 3H), 3.93 (s, 3H), 3.54-3.51 (m, 1H), 3.49-3.41 (m, 1H), 3.15-3.07 (m, 3H), 2.67-2.60 (m, 2H), 2.22-2.14 (m, 1H), 1.87-1.80 (m 1H); HPLC (method 5) 99.7% (area under the curve), t _R = 7.16 minutes; ESI + APCI MS m / z 477 [M + H] ⁺ .

Option 5

Preparation of methyl 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylate 1-2

Of the N, N '- diisopropylethylamine (N, N' -diisopropylethyl amine) 4- chloro-pyridine (10mL) -2- amine 1-1 (0.48g, 3.75mmol) was added pyrrolidine Methyl-3-carboxylic acid (0.93 g, 5.65 mmol). The reaction mixture was heated in a sealed tube at 120 ° C for 16 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between EtOAc and saturated aqueous NaHCO _3: distinguishing between (300mL 100mL). The layers were separated, the EtOAc layer was washed with brine (10 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated. The crude material was triturated with hexane, filtered and dried to give 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylic acid methyl ester 1-2 (700 mg, raw) as Off-white solid, which was used directly in the next step without further purification. ESI + APCI-MS m / z 222 [M + H] ⁺ .

1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid methyl ester (methyl 1- ( Preparation of 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidine-3-carboxylate) 1-3

At 75 ° C, 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylic acid methyl ester 1-2 (0.50 g, 2.262 mmol) and 2-bromo-1 in acetone (50 mL) were added. A mixture of-(5-chloro-2,4-dimethoxyphenyl) ethanone (0.726 g, 2.48 mmol) was heated for 16 hours. The reaction mixture was cooled to room temperature. The white precipitate formed was collected by filtration, washed with hexane (20 mL), and dried. The hydrobromide salt was suspended in saturated NaHCO ₃ solution (15.0mL), and stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and dried to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) pyrrole Alkan-3-carboxylic acid methyl ester 1-3 (0.2 g, 47%) as an off-white solid.

¹ H NMR (400MHz, CDCl ₃ ): δ 8.31 (s, 1H), 7.80 (d, J = 7.2Hz, 1H), 7.74 (s, 1H), 6.50 (s, 1H), 6.41 (s, 1H) , 6.28 (dd, J = 2.0, 7.2 Hz, 1H), 3.92 (s, 3H), 3.88 (s, 3H), 3.68 (s, 3H), 3.56 (d, J = 7.2Hz, 2H), 3.44- 3.40 (m, 1H), 3.37-3.31 (m, 1H), 3.22-3.15 (m, 1H), 2.29-2.24 (m, 2H). ESI + APCI-MS m / z 416 [M + H] ⁺ .

Preparation of 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid 1-4

For 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- in THF, CH ₃ OH and water (20 mL / 10 mL / 5 mL) 7-yl) pyrrolidine-3-carboxylic acid methyl ester 1-3 (1.0 g, 2.4 mmol) was added to LiOH‧H ₂ O (0.40 g, 9.6 mmol), and the resulting mixture was stirred at ambient temperature for 5 hours . The solvent was evaporated, the residue was diluted with water, and extracted with ethyl acetate (2 x 10 mL). The aqueous layer was acidified to pH 3 to 4 with a 10% KHSO ₄ solution. The formed precipitate was collected by filtration, washed with water and dried to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Pyrrolidine-3-carboxylic acid 1-4 (750 mg, 78%) as an off-white solid.

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.5Hz, 1H), 8.16 (s, 1H), 7.96 (s, 1H), 6.85 (s, 1H), 6.51 (d, J = 6.6Hz, 1H), 6.24 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.57-3.46 (m, 2H), 3.37-3.33 (m, 2H), 3.25-3.18 (m, 1H), 2.27-2.17 (m, 2H); ESI + APCI MS m / z 402 [M + H] ⁺ .

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) -N -methoxy- N -methylpyrrolidine- Preparation of 3-formamidine 1-5

For 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- in DMF (2.0 mL) Carboxylic acid 1-4 (200mg, 0.498mmol), N , O -dimethylhydroxylamine hydrochloride (72mg, 0.747mmol) and N , N' -diisopropylethylamine (256mg, 1.99) solution, add EDC -HCl (190 mg, 0.996 mmol) and hydroxybenzotrizol (HOBt, 152 mg, 0.996 mmol). The resulting mixture was stirred at ambient temperature for 15 hours. The reaction mixture was diluted with water, and the aqueous layer was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with water (2 x 25 mL) and then with brine, dried over anhydrous Na ₂ SO ₄ , filtered and concentrated to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazolo [1,2-a] pyridin-7-yl) -N -methoxy- N -methylpyrrolidine-3-carboxamide 1-5 (200 mg, raw). The crude material was used directly in the next step without further purification.

¹ H NMR (300 MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.95 (s, 1H), 6.85 (s, 1H), 6.51 (d, J = 7.5Hz, 1H), 6.23 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.72 (s, 3H), 3.59-3.55 (m, 2H), 3.42-3.37 (m 3H), 3.15 (s, 3H), 2.26-2.08 (m, 2H); ESI + APCI MS m / z 445 [M + H] ⁺ .

Preparation of 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxaldehyde 1-6

Add 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) -N -methoxy in anhydrous THF (500 mL) A solution of the propyl- N -methylpyrrolidine-3-carboxamide 1-5 (1.0 g, 2.25 mmol) was cooled to -78 ° C, and a LAH solution (2.0 M, 3.37 mL, 6.75 mmol) in THF was added. The resulting reaction mixture was stirred at -78 ° C for an additional hour. The reaction mixture was allowed to warm to 0 ℃ and treated with solid Na ₂ SO ₄ wet quenched, and the mixture was stirred at ambient temperature for 1 hour to produce. By passing through a pad of celite, the white solid was filtered off, which was washed with ethyl acetate (2 x 50 mL). The combined filtrates were concentrated to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxaldehyde 1 -6 (800 mg, raw), used in the next step without purification. ESI + APCI MS m / z 386 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of 2-cyclopentylethyl-1-amine 1-7a (Example 2-91)

For 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] in CH ₃ OH (5.0 mL) and CH ₂ Cl ₂ (5.0 mL) Pyridine-7-yl) pyrrolidine-3-carboxaldehyde 1-6 (150 mg, 0.389 mmol) and 2-cyclopentylethan-1-amine (66 mg, 0.584 mmol) suspension, Acetic acid (0.05 mL) was added, and the resulting mixture was stirred at room temperature for 2 hours. Then sodium cyanoborohydride (73 mg, 1.168 mmol) was added and the reaction mixture was stirred at room temperature for another 5 hours. The reaction mixture was diluted with aqueous sodium bicarbonate solution and extracted with CH ₂ Cl ₂ (2 × 10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fast-combination (silica gel, NH ₄ OH / CH ₃ OH / CH ₂ Cl ₂ 1: 9: 90) to obtain N -((1- (2- (5-chloro-2,4-di (Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-cyclopentylethyl-1-amine 1-7a (30mg, 16% ) As an off-white solid.

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.2 Hz, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.41 (dd, J = 2.4, 7.2Hz, 1H), 6.17 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.49-3.45 (m, 1H), 3.41-3.35 (m, 1H), 3.31 ( q, J = 8.4Hz, 1H), 3.01 (t, J = 8.0Hz, 1H), 2.63 (d, J = 7.6Hz, 2H), 2.57 (t, J = 7.6Hz, 2H), 2.49-2.43 ( m, 1H), 2.18-2.11 (m, 1H), 1.74-1.45 (m, 10H), 1.10-1.01 (m, 2H); HPLC (Method 4) 93.0% (area under the curve), t _R = 6.85 minutes ; ESI + APCI MS m / z 483 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of cyclohexylmethyl) methylamine 1-7b (Example 2-53)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde ) -2-cyclopentylethyl-1-amine 1-7a, 1- (1- (2- (5-chloro-2,4-dimethoxy) was prepared in the same manner using cyclohexylmethanamine phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (cyclohexylmethyl) methanamine 1-7b, and to obtain (8% yield as an off white solid ).

¹ H NMR (400 MHz, CD ₃ OD) δ: 8.00 (d, J = 7.2 Hz, 1 H), 7.93 (s, 1 H), 7.79 (s, 1 H), 6.67 (s, 1 H), 6.41 (dd, J = 2.0, 7.2Hz, 1H), 6.16 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.49-3.44 (m, 1H), 3.38-3.35 (m, 1H), 3.31- 3.26 (m, 1H), 3.00-2.96 (m, 1H), 2.68 (d, J = 7.6Hz, 2H), 2.51-2.48 (m, 1H), 2.46 (d, J = 6.8Hz, 2H), 2.19 -2.12 (m, 1H), 1.72-1.46 (m, 7H), 1.30-1.09 (m, 3H), 0.91-0.79 (m, 2H); HPLC (method 7) 98.6% (area under the curve), t _R = 7.39 minutes; ESI + APCI MS m / z 483 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of cycloheptylamine 1-7c (Example 2-32)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde N -((1- (2- (5-chloro-2,4-dimethoxy) using the same method as cycloheptanamine) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cycloheptylamine 1-7c and obtained as an off-white solid (12% yield).

¹ H NMR (400 MHz, CD ₃ OD) δ: 8.01 (d, J = 7.2 Hz, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.42 (dd, J = 2.4, 7.6Hz, 1H), 6.17 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.50-3.46 (m, 1H), 3.41-3.36 (m, 1H), 3.31- 3.24 (m, 1H), 3.01-2.96 (m, 1H), 2.67 (d, J = 6.8Hz, 1H), 2.65-2.64 (m, 1H), 2.47-2.40 (m, 1H), 2.19-2.12 ( m, 1H), 1.87-1.81 (m, 2H), 1.71-1.60 (m, 3H), 1.54-1.32 (m, 9H); HPLC (Method 4) 93.3% (area under the curve), t _R = 6.70 minutes ; ESI + APCI MS m / z 483 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Cyclopeptylmethyl) methylamine (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) -N -(cycloheptylmethyl) methanamine) 1-7d (Example 2-49)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde ) -2-cyclopentylethyl-1-amine 1-7a, 1- (1- (2- (5-chloro-2,4-dimethoxy) was prepared using cycloheptylmethanamine phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (cycloheptylmethyl) methanamine 1-7d, and to obtain an off-white solid (yield twenty four%).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.6 Hz, 1H), 7.96 (s, 1H), 7.79 (s, 1H), 6.68 (s, 1H), 6.41 (dd, J = 2.4, 7.6Hz, 1H), 6.17 (d, J = 1.6Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.48-3.44 (m, 1H), 3.38-3.33 (m, 1H), 3.29-3.24 (m, 1H), 3.00-2.96 (m, 1H), 2.62-2.59 (m, 2H), 2.49-2.40 (m, 1H), 2.39 (d, J = 6.4Hz, 2H) , 2.17-2.09 (m, 1H), 1.72-1.35 (m, 12H), 1.18-1.11 (m, 2H); HPLC (Method 4) 98.4% (area under the curve), t _R = 6.82 minutes; ESI + APCI MS m / z 497 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of -2-cycloheptylethyl-1-amine 1-7e (Example 2-65)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a using the same method, using 2-cycloheptyethyl-1-amine (2-cycloheptylethan-1-amine) to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-cycloheptylethyl-1 -Amine 1-7e and obtained as an off-white solid (yield 7.5%).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.6 Hz, 1H), 7.95 (s, 1H), 7.77 (s, 1H), 6.67 (s, 1H), 6.40 (dd, J = 2.4, 7.6Hz, 1H), 6.16 (d, J = 1.6Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.48-3.43 (m, 1H), 3.40-3.37 (m, 1H), 3.29-3.24 (m, 1H), 2.99 (t, J = 7.6Hz, 1H), 2.64 (d, J = 7.2Hz, 1H), 2.58 (t, J = 8.0Hz, 2H), 2.48- 2.41 (m, 1H), 2.17-2.09 (m, 1H), 1.71-1.32 (m, 14H), 1.19-1.12 (m, 3H); HPLC (Method 4) 98.6% (area under the curve), t _R = 7.00 minutes; ESI + APCI MS m / z 511 [M + H] ⁺ .

N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl )-Preparation of N ⁴ , N ⁴ -dimethylcyclohexane-1,4-diamine 1-7f (Example 2-24)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a using N ¹ , N ¹ -dimethylcyclohexane-1,4-diamine ( N ¹ , N ¹ -dimethylcyclohexane-1 , 4-diamine) to prepare N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine- 3- yl) methyl) - N ^4, N ⁴ - dimethylcyclohexane-1,4-diamine 1-7f, and to obtain an off-white solid (yield 24%).

¹ H NMR (400 MHz, CD ₃ OD) δ: 8.01 (d, J = 7.2 Hz, 1 H), 7.95 (s, 1 H), 7.80 (s, 1 H), 6.68 (s, 1 H), 6.43 (dd, J = 2.4, 7.6Hz, 1H), 6.18 (d, J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.50-3.46 (m, 1H), 3.42-3.36 (m, 1H), 3.32-3.26 (m, 1H), 3.05-3.01 (m, 1H), 2.71-2.60 (m, 3H), 2.49-2.41 (m, 1H), 2.25-2.14 (m, 8H), 1.78- 1.45 (m, 9H); HPLC (method 4) 99.3% (area under the curve), t _R = 6.32 minutes; ESI + APCI MS m / z 512 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-methylpyrrolidin-3-yl) methyl) methylamine 1-7 g (Example 2-64)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde ) -2-cyclopentylethyl-1-amine 1-7a The same method was used to prepare 1- (1 using 1-methylpyrrolidin-3-yl) methanamine) -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -((1-methyl 1-7 g of pyrrolidin-3-yl) methyl) methylamine, and obtained as an off-white solid (12% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.06 (d, J = 7.6Hz, 1H), 7.86 (s, 1H), 7.82 (s, 1H), 6.70 (s, 1H), 6.50 (dd, J = 2.4, 7.6Hz, 1H), 6.19 (d, J = 2.0Hz, 1H), 3.93 (s, 3H), 3.86 (s, 3H), 3.51-3.47 (m, 1H), 3.41-3.38 (m, 1H), 3.33-3.27 (m, 1H), 3.05-2.97 (m, 2H), 2.86 (t, J = 6.8Hz, 2H), 2.75-2.64 (m, 4H), 2.61-2.55 (m, 1H) , 2.55-2.41 (m, 5H), 2.00-2.02 (m, 2H), 1.77-1.60 (m, 1H), 1.61-1.52 (m, 1H); HPLC (Method 4) 95.0% (area under the curve), t _R = 6.29 minutes; ESI + APCI MS m / z 484 [M + H] ⁺ .

1- (1- (tert-butyl) pyrrolidin-3-yl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Preparation of pyridine-7-yl) pyrrolidin-3-yl) methyl) methylamine 1-7h (Example 2-63)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a using 1- (tert-butyl) pyrrolidin-3-yl) methylamine (1- ( tert- butyl) pyrrolidin-3-yl) ) methanamine) to prepare 1- (1- (tert-butyl) pyrrolidin-3-yl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) methylamine 1-7h and obtained as an off-white solid (yield 11%).

¹ H NMR (400MHz, DMSO- d ₆ ) δ: 8.12 (d, J = 7.6 Hz, 1H), 7.87 (s, 1H), 7.79 (s, 1H), 6.73 (s, 1H), 6.60 (dd, J = 2.4, 7.6 Hz, 1H), 6.25 (d, J = 2 Hz, 1H), 3.95 (s, 3H), 3.87 (s, 3H), 3.55-3.28 (m, 6H), 3.11-3.07 (m, 1H), 2.95-2.90 (m, 1H), 2.73-2.63 (m, 4H), 2.52-2.45 (m, 2H), 2.21-2.12 (m, 2H), 1.80-1.63 (m, 2H), 1.29 ( s, 9H); HPLC (method 7) 97.6% (area under the curve), t _R = 6.42 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of -1-ethylpiperidine-4-amine 1-7i (Example 2-33)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde ) -2-Cyclopentylethyl-1-amine 1-7a Using the same method, 1-ethylpiperidin-4-amine was used to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-ethylpiperidine-4 -Amine 1-7i and obtained as an off-white solid (24% yield).

¹ H NMR (400 MHz, CD ₃ OD) δ: 7.99 (d, J = 7.6 Hz, 1H), 7.94 (s, 1H), 7.79 (s, 1H), 6.67 (s, 1H), 6.40 (dd, J = 2.4, 7.6Hz, 1H), 6.15 (d, J = 2.0Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.48-3.43 (m, 1H), 3.38-3.34 (m, 1H), 3.29 (q, J = 8.0Hz, 1H), 2.98-2.90 (m, 3H), 2.63-2.50 (m, 2H), 2.49-2.35 (m, 4H), 2.17-2.09 (m, 1H) , 2.00 (t, J = 12.0Hz, 2H), 1.88 (d, J = 12.8Hz, 2H), 1.71-1.64 (m, 1H), 1.40 (q, J = 11.6Hz, 2H), 1.03 (t, J = 7.2 Hz, 3H); HPLC (Method 4) 98.7% (area under the curve), t _R = 6.29 minutes; ESI + APCI MS m / z 498 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of -1-isopropylpiperidine-4-amine 1-7j (Example 2-27)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde ) -2-Cyclopentylethyl-1-amine 1-7a Using the same method, 1-methylpiperidin-4-amine was used to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-isopropylpiperidine- 4-amine 1-7j and obtained as an off-white solid (16% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 7.96 (d, J = 7.6Hz, 1H), 7.95 (s, 1H), 7.77 (s, 1H), 6.66 (s, 1H), 6.36 (dd, J = 2,7.2Hz, 1H), 6.12 (d, J = 1.6Hz, 1H), 3.90 (s, 3H), 3.83 (s, 3H), 3.45-3.40 (m, 1H), 3.33-3.30 (m, 1H), 3.26-3.21 (m, 1H), 2.94 (t, J = 8Hz, 1H), 2.86 (d, J = 12.0Hz, 1H), 2.68-2.56 (m, 3H), 2.41-2.31 (m, 2H), 2.19-2.08 (m, 3H), 1.86 (d, J = 12.0Hz, 2H), 1.66-1.60 (m, 3H), 1.36 (q, J = 10.8Hz, 1H), 0.99 (d, J = 6.4 Hz, 6H); HPLC (method 7) 98.0% (area under the curve), t _R = 6.33 minutes; ESI + APCI MS m / z 512 [M + H] ⁺ .

1- (tert-butyl) -N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine Preparation of 3--3-yl) methyl) piperidine-4-amine 1-7k (Example 2-35)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a The same method was used to prepare 1- (tert-butyl) piperidin-4-amine (1- ( tert- butyl) piperidin-4-amine) -(Tert-butyl) -N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine- 3-yl) methyl) piperidine-4-amine 1-7k and obtained as an off-white solid (51% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 7.99-7.96 (m, 2H), 7.79 (s, 1H), 6.67 (s, 1H), 6.38 (dd, J = 2.4, 7.6Hz, 1H), 6.15 (d, J = 2.0Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.47-3.43 (m, 1H), 3.38-3.33 (m, 1H), 3.29-3.21 (m, 1H ), 3.00-2.93 (m, 3H), 2.64-2.55 (m, 2H), 2.43-2.31 (m, 2H), 2.16-2.09 (m, 3H), 1.85 (d, J = 12.4Hz, 2H), 1.71-1.61 (m, 1H), 1.36-1.27 (m, 2H), 1.02 (s, 9H); HPLC (Method 4) 99.4% (area under the curve), t _R = 6.37 minutes; ESI + APCI-MS m / z 526 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-ethylpiperidin-4-yl) methyl) methylamine 1-7l (Example 2-36)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a The same method was used to prepare 1- (1-ethylpiperidin-4-yl) methanamine (1-ethylpiperidin-4-yl) methanamine (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -((1 -Ethylpiperidin-4-yl) methyl) methylamine 1-7l and obtained as an off-white solid (yield 25%).

¹ H NMR (400 MHz, CD ₃ OD) δ: 8.01 (d, J = 7.6 Hz, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.42 (dd, J = 1.6, 7.6Hz, 1H), 6.17 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.49 (t, J = 8.8Hz, 1H), 3.41-3.35 (m, 1H) , 3.31 (q, J = 7.6Hz, 1H), 3.02 (t, J = 8.0Hz, 1H), 2.92 (d, J = 11.2Hz, 2H), 2.61 (d, J = 6.0Hz, 2H), 2.48 -2.30 (m, 3H), 2.38 (q, J = 7.2Hz, 2H), 2.15-2.11 (m, 1H), 1.94 (t, J = 11.2Hz, 2H), 1.73-1.66 (m, 3H), 1.53-1.43 (m, 1H), 1.23-1.13 (m, 2H), 1.03 (t, J = 7.6Hz, 3H); HPLC (Method 4) 99.4% (area under the curve), t _R = 6.35 minutes; ESI + APCI MS m / z 512 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 1-isopropyl-4-yl) methyl) methylamine 1-7m (Example 2-12)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde ) -2-Cyclopentylethyl-1-amine 1-7a The same method was used to prepare (1-isopropylpiperidin-4-yl) methanamine (1 - (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (1 -Isopropyl-4-yl) methyl) methylamine 1-7m and obtained as an off-white solid (15% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2 Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 6.85 (s, 1H), 6.48-6.45 ( m, 1H), 6.18-6.16 (m, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.47-3.37 (m, 1H), 3.14-3.02 (m, 1H), 2.86-2.72 ( m, 2H), 2.64-2.56 (m, 2H), 2.33-2.29 (m, 2H), 2.19-2.10 (m, 4H), 1.74-1.71 (m, 4H), 1.48-1.32 (m, 1H), 1.16-1.08 (m, 2H), 0.98-0.86 (m, 8H); HPLC (Method 5) 91.6% (area under the curve), t _R = 6.33 minutes; ESI + APCI-MS m / z 526 [M + H ] ⁺ .

4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester ( tert -butyl 4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) ethyl) piperidine-1-carboxylate) 1-7n (Example 2-10)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a, tert-butyl 4- (2- (2-aminoethyl) piperidine-1-carboxylic acid aminoethyl) piperidine-1-carboxylate) Preparation of 4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) methyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester 1-7n and obtained as an off-white (light blue-green) solid (70% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 7.98 (d, J = 7.6Hz, 1H), 7.94 (s, 1H), 6.66 (s, 1H), 6.37 (dd, J = 2.0, 7.2Hz, 1H ), 6.13 (d, J = 2.0Hz, 1H), 3.96 (d, J = 13.2Hz, 2H) 3.91 (s, 3H), 3.84 (s, 3H), 3.45-3.41 (m, 1H), 3.37- 3.32 (m, 1H), 3.28-3.24 (m, 1H), 2.96 (d, J = 7.6Hz, 1H), 2.69-2.55 (m, 6H), 2.45-2.41 (m, 1H), 2.15- 2.07 ( m, 1H), 1.69-1.58 (m, 3H), 1.45-1.38 (m, 3H), 1.35 (s, 9H), 1.04-0.94 (m, 2H); HPLC (method 7) 99.3% (area under the curve ), T _R = 6.96 minutes; ESI + APCI MS m / z 598 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of 2- (1-methylpiperidin-4-yl) ethyl-1-amine 1-7o (Example 2-3)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a using 2- (1-methylpiperidin-4-yl) ethyl-1-amine (2- (1-methylpiperidin-4- yl) ethan-1-amine) to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrole Alk-3-yl) methyl) -2- (1-methylpiperidin-4-yl) ethyl-1-amine 1-7o and obtained as an off-white solid (yield 9.4%).

¹ H NMR (300 MHz, DMSO- d ₆ ) δ: 8.27 (d, J = 7.6 Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 6.85 (s, 1H), 6.47 (d, J = 6.6Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.46-3.41 (m, 2H), 3.27-3.13 (m, 2H), 3.08-3.02 (m, 1H), 2.72 (d, J = 11.7Hz, 1H), 2.67-2.55 (m, 3H), 2.43-2.32 (m, 3H), 2.20-2.00 (m, 4H), 1.82-1.68 (m , 3H), 1.61 (d, J = 11.7Hz, 1H), 1.35-1.30 (m, 2H), 1.25 (s, 1H), 1.16-1.06 (m, 2H); HPLC (method 4) 96.8% (curve Lower area), t _R = 6.29 minutes; ESI + APCI MS m / z 512 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of 2- (1-ethylpiperidin-4-yl) ethyl-1-amine 1-7p (Example 2-45)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a, 2- (1-ethylpiperidin-4-yl) ethyl-1-amine (2- (1-ethylpiperidin-4- yl) ethan-1-amine) to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrole Alk-3-yl) methyl) -2- (1-ethylpiperidin-4-yl) ethyl-1-amine 1-7p, and obtained as an off-white solid (92% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.01 (d, J = 7.2Hz, 1H), 7.96 (s, 1H), 7.81 (s, 1H), 6.69 (s, 1H), 6.41 (d, J = 7.2Hz, 1H), 6.17 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.49-3.451 (m, 1H), 3.41-3.37 (m, 1H), 3.44-3.42 ( m, 1H), 3.03 (t, J = 8.0Hz, 1H), 2.90 (d, J = 10.4Hz, 2H), 2.65-2.57 (m, 4H), 2.50-2.42 (m, 1H), 2.40-2.34 (m, 2H), 2.15-2.12 (m, 1H), 1.96 (t, J = 10.4 Hz, 2H), 1.72-1.65 (m, 3H) 1.45-1.43 (m, 2H), 1.41-1.39 (m, 1H), 1.24-1.18 (m, 2H), 1.03 (t, J = 7.2Hz, 3H); HPLC (Method 4) 96.7% (area under the curve), t _R = 6.34 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of 2- (1-propylpiperidin-4-yl) ethyl-1-amine 1-7q (Example 2-44)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a using 2- (1-propylpiperidin-4-yl) ethyl-1-amine (2- (1-propylpiperidin-4- yl) ethan-1-amine) to prepare N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrole Alk-3-yl) methyl) -2- (1-propylpiperidin-4-yl) ethyl-1-amine 1-7q and obtained as an off-white solid (yield 28%).

¹ H NMR (400MHz, CD ₃ OD) δ: 7.99 (d, J = 7.6Hz, 1H), 7.95 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.40 (dd, J = 2.4, 7.6Hz, 1H), 6.16 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.48-3.44 (m, 1H), 3.40-3.35 (m, 1H), 3.31- 3.24 (m, 1H), 3.01-2.97 (m, 1H), 2.89 (d, J = 11.6Hz, 2H), 2.64-2.56 (m, 4H), 2.49-2.41 (m, 1H), 2.27-2.23 ( m, 2H), 2.17-2.11 (m, 1H), 1.98 (t, J = 12.0Hz, 2H), 1.73-1.63 (m, 3H) 1.47-1.38 (m, 4H), 1.37-1.18 (m, 3H ), 0.83 (t, J = 7.6 Hz, 3H); HPLC (Method 4) 98.1% (area under the curve), t _R = 6.24 minutes; ESI + APCI MS m / z 540 [M + H] ⁺ .

4- (3-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Preparation of methyl) amino) propyl) piperidine-1-carboxylic acid tert-butyl ester 1-7r (Example 2-92);

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde yl) -2-cyclopentyl-1-amine in the same manner 1-7a, 4- (3-aminopropyl) piperidine-1-carboxylate (tert -butyl 4- (3- aminopropyl) piperidine-1-carboxylate) Preparation of 4- (3-(((1- (2- (2-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) methyl) amino) propyl) piperidine-1-carboxylic acid tert-butyl ester 1-7r, and obtained as an off-white solid (12% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.01 (d, J = 7.2Hz, 1H), 7.95 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.42 (d, J = 7.6Hz, 1H), 6.18 (s, 1H), 3.97 (d, J = 19.6Hz, 2H) 3.92 (s, 3H), 3.85 (s, 3H), 3.49 (t, J = 8.4Hz, 1H) , 3.42-3.35 (m, 1H), 3.33-3.24 (m, 1H), 3.02 (t, J = 7.6Hz, 1H), 2.66-2.42 (m, 6H), 2.20-2.10 (m, 1H), 1.75 -1.65 (m, 1H), 2.39 (d, J = 12.0Hz, 2H), 1.55-1.45 (m, 2H), 1.40-1.25 (m, 11H), 1.25-1.13 (m, 2H), 1.00-0.93 (m, 2H); HPLC (Method 4) 92.6% (area under the curve), t _R = 6.97 minutes; ESI + APCI MS m / z 612 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde yl) amino) methyl) piperidine-1-carboxylate (tert -butyl 3 - ((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ) pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate) 1-7s (Example 2-48)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde yl) -2-cyclopentyl-1-amine in the same manner 1-7a, using 3- (aminomethyl) piperidine-1-carboxylate (tert -butyl 3- (aminomethyl) piperidine- 1-carboxylate) Preparation of 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine- 3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 1-7s and obtained as an off-white solid (yield 6%).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.2 Hz, 1H), 7.93 (s, 1H), 7.79 (s, 1H), 6.67 (s, 1H), 6.42 (dd, J = 2.0, 7.2Hz, 1H), 6.16 (d, J = 2Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.77-3.69 (m, 1H), 3.48-3.44 (m, 1H ), 3.30-3.24 (m, 2H), 3.02-2.97 (m, 1H), 2.90-2.79 (m, 1H), 2.63-2.54 (m, 3H), 2.49-2.39 (m, 3H), 2.18-2.09 (m, 1H), 1.82-1.54 (m, 4H), 1.40-1.39 (m, 1H), 1.30 (s, 9H), 1.16-1.11 (m, 2H); HPLC (method 7) 99.2% (under the curve Area), t _R = 7.46 minutes; ESI + APCI MS m / z 584 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-methylpiperidin-3-yl) methyl) methylamine 1-7t (Example 2-70)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a The same method was used to prepare 1- (1-methylpiperidin-3-yl) methanamine (1-methylpiperidin-3-yl) methanamine (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -((1 -Methylpiperidin-3-yl) methyl) methylamine 1-7t and obtained as an off-white solid (yield 11%).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.6 Hz, 1H), 7.95 (s, 1H), 7.79 (s, 1H), 6.68 (s, 1H), 6.42 (dd, J = 2.4, 7.6Hz, 1H), 6.16 (d, J = 2.0Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.48 (t, J = 8.4Hz, 1H), 3.40-3.34 (m, 1H), 3.30-3.23 (m, 2H), 3.01 (t, J = 8.0Hz, 1H), 2.87 (d, J = 10Hz, 1H), 2.75 (d, J = 10.8Hz, 1H), 2.62-2.53 (m, 2H), 2.48-2.40 (m, 3H), 2.18 (d, J = 2.4Hz, 3H), 2.18-2.10 (m, 1H), 1.90-1.82 (m, 1H), 1.76- 1.45 (m, 5H), 0.90-0.79 (m, 1H); HPLC (method 7) 97.6% (area under the curve), t _R = 6.34 minutes; ESI + APCI MS m / z 498 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-ethylpiperidin-3-yl) methyl) methylamine 1-7u (Example 2-71)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a In the same manner, (1-ethylpiperidin-3-yl) methanamine was used to prepare 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -((1 -Ethylpiperidin-3-yl) methyl) methylamine 1-7u and obtained as an off-white solid (yield 11%).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.02 (d, J = 7.2Hz, 1H), 7.92 (s, 1H), 7.80 (s, 1H), 6.69 (s, 1H), 6.44 (dd, J = 2.0, 7.2Hz, 1H), 6.17 (d, J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.49 (t, J = 8.4Hz, 1H), 3.38-3.35 (m, 1H), 3.29 (q, J = 9.2Hz, 1H), 3.08-2.95 (m, 3H), 2.65-2.61 (m, 2H), 2.53-2.45 (m, 5H), 2.18-2.10 (m , 1H), 2.07-1.99 (m, 1H), 1.78-1.67 (m, 5H), 1.61-1.50 (m, 1H), 1.09-1.04 (m, 3H), 0.99-0.90 (m, 1H); HPLC (Method 4) 98.0% (area under the curve), t _R = 6.33 minutes; ESI + APCI MS m / z 512 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-isopropylpiperidin-3-yl) methyl) methylamine 1-7v (Example 2-72)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a The same method was used to prepare (1-isopropylpiperidin-3-yl) methanamine (1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(( 1-Isopropylpiperidin-3-yl) methyl) methylamine 1-7v and obtained as an off-white solid (yield 11%).

¹ H NMR (400MHz, CD ₃ OD) δ: 7.99 (d, J = 7.6Hz, 1H), 7.94 (s, 1H), 7.78 (s, 1H), 6.67 (s, 1H), 6.39 (dd, J = 2.0, 7.2Hz, 1H), 6.14 (d, J = 1.6Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.46 (t, J = 8.4Hz, 1H), 3.39-3.34 (m, 1H), 3.29 (q, J = 8.0Hz, 1H), 3.02-2.96 (m, 2H), 2.89 (d, J = 11.6Hz, 1H), 2.81-2.73 (m, 1H), 2.63- 2.52 (m, 2H), 2.49-2.39 (m, 3H), 2.12-2.09 (m, 2H), 1.91 (t, J = 11.2Hz, 1H), 1.81-1.63 (m, 4H), 1.59-1.49 ( m, 1H), 1.04-1.02 (m, 6H), 0.95-0.82 (m, 1H); HPLC (method 7) 97.6% (area under the curve), t _R = 6.39 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

4-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl ) Amine) Preparation of azacycloheptane-1-carboxylic acid tert-butyl ester 1-7w (Example 2-54)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde yl) -2-cyclopentyl-1-amine in the same manner 1-7a, using 4-amino-azepan-l-carboxylate (tert -butyl 4-aminoazepane-1 -carboxylate) Preparation of 4-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl (Amino) amino) azacycloheptane-1-carboxylic acid tert-butyl ester 1-7w and obtained as an off-white solid (8% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.6 Hz, 1H), 7.94 (s, 1H), 7.79 (s, 1H), 6.68 (s, 1H), 6.41 (dd, J = 2.4, 7.6Hz, 1H), 6.16 (d, J = 1.6Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.48-3.44 (m, 2H), 3.39-3.26 (m, 4H), 3.24-3.11 (s, 1H), 3.00 (t, J = 8.4Hz, 1H), 2.64 (d, J = 6.8Hz, 2H), 2.59-2.49 (m, 1H), 2.42-2.38 (m , 1H), 2.15-2.11 (m, 1H), 1.96-1.93 (m, 1H), 1.87-1.71 (m, 2H), 1.70-1.65 (m, 1H), 1.52-1.40 (m, 2H), 1.31 (s, 9H), 1.30-1.18 (m, 1H); HPLC (method 7) 99.3% (area under the curve), t _R = 6.89 minutes; ESI + APCI MS m / z 584 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) Preparation of 2-phenylethyl-1-amine 1-7x (Example 2-1)

With N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde Group) -2-cyclopentylethyl-1-amine 1-7a using the same method to prepare N -((1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-phenylethyl-1-amine 1-7x and obtained as an off-white solid (15% yield).

¹ H NMR (400MHz, DMSO- d ₆ ) δ: 8.36 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.94 (s, 1H), 7.30-7.18 (m, 5H), 6.85 ( s, 1H), 6.46 (dd, J = 2.4, 7.6 Hz, 1H), 6.18 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.43-3.31 (m, 1H), 3.40 -3.39 (m, 1H), 3.38-3.36 (m, 1H), 3.10-3.0 (m, 1H), 2.77-2.72 (m, 4H), 2.67-2.55 (m, 2H), 2.50-2.45 (m, 1H), 2.15-2.0 (m, 1H), 1.65-1.60 (m, 1H); HPLC (Method 4) 96.6% (area under the curve), t _R = 6.72 minutes; ESI + APCI MS m / z 491 [M + H] ⁺ .

Option 6

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl-1- Ketone (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) ethan-1-one) 1-8 Preparation

At ambient temperature, 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) in anhydrous THF (500 mL) -A solution of N -methoxy- N -methylpyrrolidine-3-carboxamide 1-5 (500 mg, 1.12 mmol) was added to a CH ₃ MgBr solution (2.0 M, 1.12 mL, 3.37 mmol) in DEE. The resulting reaction mixture was stirred at ambient temperature for an additional 3 hours. The reaction mixture was cooled to 0 ° C., quenched with aqueous NH ₄ Cl solution, and the aqueous layer was extracted with ethyl acetate (2 × 50 mL). The combined organic layers were dried over anhydrous Na ₂ SO ₄ , filtered and concentrated to give 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) pyrrolidin-3-yl) ethan-1-one 1-8 (350 mg, raw). The crude product was used directly in the next step without further purification. ESI + APCI MS m / z 400 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 2-cyclopentylethyl) ethyl-1-amine 1-9a (Example 2-87)

For 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) in CH ₃ OH (5.0 mL) Pyrrolidin-3-yl) ethan-1-one 1-8 (150 mg, 0.375 mmol) and 2-cyclopentylethan-1-amine (63 mg, 0.563 mmol) suspension were added Acetic acid (0.05 mL), and the resulting mixture was stirred at 80 ° C for 12 hours. To the reaction mixture was added sodium cyanoborohydride (71 mg, 1.12 mmol), and the reaction mixture was stirred at 80 ° C. for an additional 6 hours. The reaction mixture was cooled to room temperature, diluted with an aqueous sodium bicarbonate solution, and extracted with CH ₂ Cl ₂ (2 × 10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification of the residue by combination-rapid concomitant (silicone, NH ₄ OH / CH ₃ OH / CH ₂ Cl ₂ : 1: 9: 90) gave 1- (1- (2- (5-chloro-2,4 - dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (2- cyclopentylethyl) ethan-l-amine 1-9a (30 mg, 16%) as an off-white solid.

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.2 Hz, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.41 (d, J = 7.2Hz, 1H), 6.16 (s, 1H), 3.92 (s, 3H), 3.84 (s, 3H), 3.53 (t, J = 8.4Hz, 1H), 3.45-3.35 (m, 1H), 3.31 -3.21 (m, 1H), 3.04 (t, J = 8.8Hz, 1H), 2.67-2.60 (m, 2H), 2.53-2.46 (m, 1H), 2.30-2.20 (m, 1H), 2.10-2.03 (m, 1H), 1.78-1.63 (m, 4H), 1.60-1.41 (m, 6H), 1.06 (d, J = 6.0Hz, 5H); HPLC (Method 4) 94.9% (area under the curve), t _R = 6.93 minutes; ESI + APCI MS m / z 497 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of cycloheptylmethyl) ethyl-1-amine 1-9b (Example 2-88)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a The same method was used to prepare 1- (1- (2- (5-chloro-2,4-dimethoxy) using cycloheptylmethylamine phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (cycloheptylmethyl) ethan-l-amine 1-9b, and to obtain an off-white solid ( 15% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.01 (d, J = 7.6Hz, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.41 (d, J = 7.2Hz, 1H), 6.16 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.53-3.35 (m, 2H), 3.30-3.20 (m, 1H), 3.06-2.97 ( m, 1H), 2.61 (q, J = 6.4Hz, 1H), 2.48-2.40 (m, 1H), 2.36-2.05 (m, 3H), 1.70-1.35 (m, 12H), 1.18-1.10 (m, 2H), 1.05 (d, J = 6.0 Hz, 3H); HPLC (method 4) 99.8% (area under the curve), t _R = 6.93 minutes; ESI + APCI MS m / z 511 [M + H] ⁺ .

^{N 1 - (1- (1- (} 2- (5- chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) - N ^4, N ⁴ - dimethylcyclohexane-1,4-diamine 1-9c (Example 2-94)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N - (2-cyclopentylethyl) ethan-l-amine in the same manner 1-9a, using N ^1, N ¹ - dimethylcyclohexane-1,4-diamine preparation of N ¹ - (1- ( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) -N ⁴ , N ⁴ -dimethylcyclohexane-1,4-diamine 1-9c and obtained as an off-white solid (yield 15%).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.10 (d, J = 7.2Hz, 1H), 8.05 (s, 1H), 7.89 (s, 1H), 6.78 (s, 1H), 6.52 (d, J = 7.2Hz, 1H), 6.26 (s, 1H), 4.01 (s, 3H), 3.94 (s, 3H), 3.52-3.45 (m, 2H), 3.40-3.32 (m, 1H), 3.14 (t, J = 8.8Hz, 1H), 2.92 (s, 1H), 2.75 (t, J = 6.0Hz, 1H), 2.35-2.25 (m, 9H), 1.98-1.95 (m, 1H), 1.86-1.80 (m , 2H), 1.73 (s, 1H), 1.68-1.60 (m, 4H), 1.52-1.46 (m, 1H), 1.17 (d, J = 6.4Hz, 3H); HPLC (method 4) 99.6% (curve Lower area), t _R = 6.39 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

3-(((((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- (Ethyl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 1-9d (Example 2-113)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N - (2-cyclopentylethyl) ethan-l-amine in the same manner 1-9a, using 3- (aminomethyl) pyrrolidine-1-carboxylate (tert -butyl 3- (aminomethyl) pyrrolidine-1-carboxylate ) Preparation of 3-((((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Methyl) pyrrolidin-3-yl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 1-9d and obtained as an off-white solid (yield 10%).

¹ H NMR (400MHz, CD ₃ OD) δ: 7.99 (d, J = 7.6Hz, 1H), 7.95 (s, 1H), 7.79 (s, 1H), 6.68 (s, 1H), 6.40 (dd, J = 2.4, 7.6Hz, 1H), 6.14 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.51-3.31 (m, 4H), 3.27-3.23 (m, 1H), 3.05- 2.90 (m, 2H), 2.66-2.10 (m, 6H), 2.05-1.90 (m, 2H), 1.73-1.62 (m, 1H), 1.58-1.47 (m, 1H), 1.36 (s, 9H), 1.04 (d, J = 6.0 Hz, 3H); HPLC (method 4) 94.8% (area under the curve), t _R = 6.81 minutes; ESI + APCI MS m / z 584 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-isopropylpyrrolidin-3-yl) methyl) ethyl-1-amine 1-9e (Example 2-108)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a Same method using (1-isopropylpyrrolidin-3-yl) methanamine preparation of 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ((1-Isopropylpyrrolidin-3-yl) methyl) ethan-1-amine 1-9e was obtained as an off-white solid (yield 7.6%).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.6 Hz, 1H), 7.95 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.41 (dd, J = 1.6, 7.2Hz, 1H), 6.16 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.51-3.35 (m, 2H), 3.30-3.23 (m, 1H), 3.06- 2.89 (m, 2H), 2.76-2.69 (m, 1H), 2.66-2.52 (m, 3H), 2.50-2.36 (m, 2H), 2.31-2.14 (m, 4H), 2.05-1.92 (m, 1H ), 1.73-1.62 (m, 1H), 1.50-1.40 (m, 1H), 1.08-1.03 (m, 9H); HPLC (Method 4) 93.4% (area under the curve), t _R = 6.39 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

N- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl Preparation of 1-ethyl) -1-ethylpiperidine-4-amine 1-9f (Example 2-82)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a Using the same method to prepare N- (1- (1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) -1-ethylpiperidine-4-amine 1-9f And obtained as an off-white solid (yield 15%).

¹ H NMR (400MHz, CD ₃ OD) δ: 8.00 (d, J = 7.6 Hz, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.42 (dd, J = 2.4,7.6Hz, 1H), 6.16 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.54 (t, J = 8.8Hz, 1H), 3.43-3.37 (m, 2H) , 3.30-3.20 (m, 1H), 3.05-3.00 (m, 1H), 2.89 (d, J = 10.4Hz, 2H), 2.74-2.67 (m, 1H), 2.60-2.52 (m, 1H), 2.39 (q, J = 7.2Hz, 2H), 2.25-2.14 (m, 1H), 2.14-1.85 (m, 3H), 1.82-1.65 (m, 2H), 1.45-1.35 (m, 1H), 1.30-1.20 (m, 1H), 1.04-0.99 (m, 6H); HPLC (method 4) 99.5% (area under the curve), t _R = 6.35 minutes; ESI + APCI MS m / z 512 [M + H] ⁺ .

1- (t-butyl) - N - (1- (1- (2- (5- chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) Preparation of pyrrolidin-3-yl) ethyl) piperidine-4-amine 1-9g (Example 2-109)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N - (2-cyclopentylethyl) ethan-l-amine in the same manner 1-9a, using 1- (tert-butyl) piperidin-4-amine 1- (tert-butyl) - N - (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) piperidine- 1-9 g of 4-amine was obtained as an off-white solid (yield 10%).

¹ H NMR (400 MHz, CD ₃ OD) δ: 7.99 (d, J = 7.6 Hz, 1H), 7.96 (s, 1H), 7.79 (s, 1H), 6.68 (s, 1H), 6.40 (dd, J = 2.0, 7.6Hz, 1H), 6.15 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.52-3.37 (m, 2H), 3.28-3.23 (m, 1H), 3.03- 2.97 (m, 3H), 2.74-2.66 (m, 1H), 2.53-2.47 (m, 1H), 2.23-2.02 (m, 4H), 1.93-1.77 (m, 2H), 1.73-1.65 (m, 1H ), 1.40-1.30 (m, 1H), 1.29-1.15 (m, 1H), 1.17 (d, J = 4.8Hz, 3H), 1.02 (s, 9H); HPLC (method 4) 96.9% (area under the curve ), T _R = 6.40 minutes; ESI + APCI MS m / z 540 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-methylpiperidin-4-yl) methyl) ethyl-1-amine 1-9h (Examples 2-100);

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a, prepared using (1-methylpiperidin-4-yl) methanamine in the same method 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( (1-methylpiperidin-4-yl) methyl) ethyl-1-amine 1-9h and obtained as an off-white solid (15% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 7.99 (d, J = 7.2Hz, 1H), 7.96 (s, 1H), 7.79 (s, 1H), 6.68 (s, 1H), 6.40 (dd, J = 2.0, 7.2Hz, 1H), 6.15 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.52 (t, J = 8.0Hz, 1H), 3.40 (t, J = 9.6Hz , 1H), 3.28 (q, J = 9.6Hz, 1H), 3.05 (t, J = 9.2Hz, 1H), 2.82 (d, J = 11.6Hz, 2H), 2.57-2.46 (m, 2H), 2.39 -2.34 (m, 1H), 2.25-2.19 (m, 1H), 2.19 (s, 3H), 2.07-2.01 (m, 1H), 1.97-1.91 (m, 2H), 1.75-1.61 (m, 3H) , 1.42-1.32 (m, 1H), 1.23-1.13 (m, 2H), 1.05 (d, J = 6.4 Hz, 3H); HPLC (method 7) 95.9% (area under the curve), t _R = 6.29 minutes; ESI + APCI MS m / z 512 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-ethylpiperidin-4-yl) methyl) ethyl-1-amine 1-9i (Example 2-83)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a The same method, using (1-ethylpiperidin-4-yl) methylamine to prepare 1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -((1-ethylpiperidin-4-yl) Methyl) ethyl-1-amine 1-9i and obtained as an off-white solid (25% yield).

¹ H NMR (400 MHz, CD ₃ OD) δ: 8.01 (d, J = 7.6 Hz, 1H), 7.96 (s, 1H), 7.80 (s, 1H), 6.68 (s, 1H), 6.42 (dd, J = 2.4, 7.6Hz, 1H), 6.16 (d, J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.53 (t, J = 8.0Hz, 1H), 3.42-3.36 (m, 1H), 3.29-3.23 (m, 1H), 3.07 (t, J = 9.2Hz, 1H), 2.94 (d, J = 11.6Hz, 2H), 2.61-2.48 (m, 2H), 2.40- 2.34 (m, 3H), 2.28-2.18 (m, 1H), 2.08-2.02 (m, 1H), 1.95-1.89 (m, 2H), 1.77-1.63 (m, 3H), 1.44-1.39 (m, 1H ), 1.24-1.14 (m, 2H), 1.05 (d, J = 6.4Hz, 3H), 1.02 (t, J = 7.2Hz, 3H); HPLC (method 8) 99.5% (area under the curve), t _R = 6.40 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

4- (2-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3 -Yl) ethyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester 1-9j (Example 2-93)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a The same method was used to prepare 4- (2- (4- (2-aminoethyl) piperidine-1-carboxylic acid tert-butyl ester) (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) Amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester 1-9j and obtained as an off-white solid (13% yield).

¹ H NMR (400 MHz, CD ₃ OD) δ: 8.11 (d, J = 7.6 Hz, 1H), 8.05 (d, J = 0.8 Hz, 1H), 7.90 (s, 1H), 6.78 (s, 1H), 6.52 (dd, J = 2.0, 7.6 Hz, 1H), 6.26 (d, J = 2.0 Hz, 1H), 4.06 (d, J = 17.6 Hz, 2H), 4.01 (s, 3H), 3.94 (s, 3H ), 3.62-3.45 (m, 2H), 3.40-3.32 (m, 1H), 3.16-3.08 (m, 1H), 2.82-2.60 (m, 5H), 2.40-2.32 (m, 1H), 2.30-2.15 (m, 1H), 1.86-1.76 (m, 1H), 1.72 (d, J = 12.4Hz, 2H), 1.60-1.42 (m, 12H), 1.17 (d, J = 6.4Hz, 3H), 1.08 ( d, J = 12.8 Hz, 2H); HPLC (Method 4) 91.9% (area under the curve), t _R = 6.93 minutes; ESI + APCI MS m / z 612 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 2- (1-propylpiperidin-4-yl) ethyl) ethyl-1-amine 1-9k (Example 2-101)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a The same method was used to prepare 1- (1- (2 - (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (2- (1- propyl Piperidin-4-yl) ethyl) ethyl-1-amine 1-9k and obtained as an off-white solid (12% yield).

¹ H NMR (300 MHz, DMSO- d ₆ ) δ: 8.00 (d, J = 7.2 Hz, 1H), 7.96 (s, 1H), 7.79 (s, 1H), 6.81 (s, 1H), 6.40 (dd, J = 2.4, 5.2Hz, 1H), 6.15 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.50-3.34 (m, 2H), 3.26 (d, J = 7.2Hz, 1H ), 3.01-2.97 (m, 1H), 2.84 (d, J = 11.6Hz, 2H), 2.68-2.52 (m, 2H), 2.48-2.42 (m, 1H), 2.30-2.14 (m, 4H), 1.92-1.80 (m, 2H), 1.77-1.66 (m, 1H), 1.62 (d, J = 10.8Hz, 2H), 1.47-1.32 (m, 4H), 1.26-1.13 (m, 3H), 1.04 ( d, J = 6.4 Hz, 3H) 0.82 (q, J = 8.0 Hz, 3H); HPLC (method 7) 97.9% (area under the curve), t _R = 6.36 minutes; ESI + APCI MS m / z 554 [M + H] ⁺ .

4- (3-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Ethyl) amino) propyl) piperidine-1-carboxylic acid tert-butyl ester ( tert -butyl 4- (3-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) Preparation of imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) propyl) piperidine-1-carboxylate) 1-9l (Example 2-99)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a, 4- (3- (4- (3-aminopropyl) piperidine-1-carboxylic acid tert-butyl ester) ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino ) Propyl) piperidine-1-carboxylic acid tert-butyl ester 1-9l and obtained as an off-white solid (12% yield).

¹ H NMR (400 MHz, CD ₃ OD) δ: 8.01 (d, J = 7.6 Hz, 1H), 7.95 (d, J = 1.6 Hz, 1H), 7.80 (s, 1H), 6.69 (s, 1H), 6.42 (dd, J = 2.0, 5.6 Hz, 1H), 6.17 (d, J = 1.6 Hz, 1H), 3.97 (d, J = 18.8 Hz, 2H), 3.92 (s, 3H), 3.85 (s, 3H ), 3.52-3.36 (m, 2H), 3.31-3.23 (m, 1H), 3.06-2.98 (m, 1H), 2.72-2.60 (m, 3H), 2.55-2.49 (m, 1H), 2.35-2.02 (m, 2H), 1.77-1.64 (m, 1H), 1.63 (d, J = 12.4Hz, 2H), 1.57-1.42 (m, 2H), 1.40-1.30 (m, 11H), 1.24-1.16 (m , 2H), 1.08 (d, J = 6.0 Hz, 3H), 1.01-0.92 (m, 2H); HPLC (method 4) 96.9% (area under the curve), t _R = 7.00 minutes; ESI + APCI MS m / z 626 [M + H] ⁺ .

3-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl ) Amino) methyl) piperidine-1-carboxylic acid tert-butyl ester ( tert -butyl 3-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a ] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) methyl) piperidine-1-carboxylate) 1-9m (Example 2-98)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-Cyclopentylethyl) ethyl-1-amine 1-9a The same method was used to prepare 3-(((1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) methyl) piper Pyridine-1-carboxylic acid tert-butyl ester was 1-9 m and was obtained as an off-white solid (13% yield).

¹ H NMR (400MHz, CD ₃ OD) δ: 7.98 (d, J = 7.2Hz, 1H), 8.94 (s, 1H), 7.78 (s, 1H), 6.67 (s, 1H), 6.40 (d, J = 5.6Hz, 1H), 6.14 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.80-3.73 (m, 1H), 3.55-3.32 (m, 2H), 3.28-3.20 ( m, 1H), 3.06-2.94 (m, 1H), 2.59-2.47 (m, 3H), 2.39-2.13 (m, 3H), 2.08-2.00 (m, 1H), 1.82-1.63 (m, 2H), 1.60-1.50 (m, 2H), 1.40-20 (m, 11H), 1.17-1.10 (m, 1H), 1.03 (d, J = 4.0Hz, 3H); HPLC (Method 4) 98.1% (area under the curve ), T _R = 6.92 minutes; ESI + APCI MS m / z 598 [M + H] ⁺ .

Option 7

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4-carboxylic acid (1- (2- ( Preparation of 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidine-4-carboxylic acid) 2-2

For 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- in THF, CH ₃ OH and water (20 mL / 10 mL / 5 mL) A solution of 7-yl) piperidine-4-carboxylic acid ethyl ester 2-1 (1.00 g, 2.25 mmol) was added LiOH · H ₂ O (140 mg, 3.37 mmol), and the resulting mixture was stirred at ambient temperature for 5 hours. The solvent was evaporated and the residue was diluted with water and extracted with ethyl acetate (2 x 10 mL). The aqueous layer was acidified to pH 3 to 4 with a 10% KHSO ₄ solution. The formed precipitate was collected by filtration, washed with water and dried to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidine-4-carboxylic acid 2-2 (750 mg, 80%) as an off-white solid. ESI + APCI-MS m / z 416 [M + H] ⁺ .

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) -N -methoxy- N -methylpiperidine- 4-Methylamine (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) -N -methoxy- N -methylpiperidine-4-carboxamide) 2 Preparation of -3

1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4-carboxylate in DMF (10 mL) Acid 2-2 (700mg, 1.68mmol), N , O -dimethylhydroxylamine hydrochloride (327mg, 3.37mmol) and N , N' -diisopropylethylamine (1.55g, 8.4mmol) suspension, HATU (1.6 g, 4.2 mmol) was added. The resulting mixture was stirred at ambient temperature for 15 hours. The reaction mixture was quenched with water, and the aqueous layer was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with water and brine, dried over Na ₂ SO ₄ , filtered and concentrated to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridin-7-yl) -N -methoxy- N -methylpiperidine-4-carboxamide 2-3 (600 mg, 83%) as an off-white solid. ESI + APCI MS m / z 459 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl-1- Ketone (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4-yl) ethan-1-one) 2-4 Preparation

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl)-in THF (50 mL) cooled to 0 ° C A solution of N -methoxy- N -methylpiperidine-4-carboxamide 2-3 (1.00 g, 2.17 mmol) was added dropwise to CH ₃ MgBr (3.0 in diethyl ether) M, 2.9 mL, 6.51 mmol). The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was quenched with aqueous NH ₄ Cl solution, and the aqueous layer was extracted with ethyl acetate (2 × 50 mL). The organic layer was washed with water and brine, dried over Na ₂ SO _4, filtered and concentrated. The residue was purified by combi-rapid color chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to obtain 1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethan-1-one 2-4 (800 mg, 89%), as Light yellow solid.

¹ H NMR (400MHz, CD ₃ OD): δ 8.02 (d, J = 7.6Hz, 1H), 7.95 (s, 1H), 7.85 (s, 1H), 6.67 (d, J = 3.6Hz, 1H), 6.65 (d, J = 2.4Hz, 1H), 6.56 (d, J = 2.0Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.75-3.72 (m, 2H), 2.80-2.73 (m, 2H), 2.57-2.50 (m, 1H), 2.12 (s, 3H), 1.91 (d, J = 13.2Hz, 2H), 1.63-1.53 (m, 2H), ESI + APCI MS m / z 414 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of cyclopentylmethyl) ethyl-1-amine 2-6a (Example 2-112)

P- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine in CH ₃ OH (5 mL) A suspension of pyridin-4-yl) ethan-1-one 2-4 (150 mg, 0.36 mmol) and cyclopentylmethanamine (cyclopentylmethanamine) 2-5a (35 mg, 0.36 mmol) was added to acetic acid (0.1 mL). The resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (114 mg, 1.81 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with an aqueous sodium bicarbonate solution (20 mL), and the aqueous layer was extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined were washed with brine (20mL) The organic extracts were dried over Na ₂ SO _4, filtered and concentrated. The residue was purified by combinatorial-fast chromatography [silica gel; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9) to obtain 1- (1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (cyclopentylmethyl) ethan-l-amine 2- 6a (60 mg, 36% yield) as an off-white solid.

¹ H NMR (400MHz, CD ₃ OD): δ 8.00 (d, J = 7.2Hz, 1H), 7.97 (s, 1H), 7.84 (s, 1H), 6.67 (s, 1H), 6.64 (dd, J = 2.4, 7.6Hz, 1H), 6.55 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.77 (d, J = 12.4Hz, 2H), 2.68-2.61 (m, 2H) , 2.55-2.38 (m, 3H), 1.98-1.90 (m, 1H), 1.72-1.69 (m, 4H), 1.57-1.46 (m, 5H) 1.39-1.30 (m, 2H), 1.14-1.06 (m , 2H), 0.96 (d, J = 6.8Hz, 3H); HPLC (method 11) 98.9% (area under the curve), t _R = 7.35 minutes; ESI + APCI-MS m / z 497 [M + H] ⁺ .

3-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester ( tert -butyl 3-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2- a ] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) pyrrolidine-1-carboxylate) 2-6b (Example 2-106)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a The same method was used to prepare 3-((((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) Methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 2-6b was obtained as an off-white solid (yield 45%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.00 (d, J = 7.6Hz, 1H), 7.96 (s, 1H), 7.84 (s, 1H), 6.67 (s, 1H), 6.64 (dd, J = 2.0, 7.6Hz, 1H), 6.55 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.77 (d, J = 12.8Hz, 2H), 3.45-3.30 (m, 2H) , 2.92-2.86 (m, 1H), 2.67-2.44 (m, 5H), 2.24-2.23 (d, J = 5.2Hz, 1H), 1.95-1.91 (m, 1H) 1.75-1.68 (m, 2H), 1.51-1.49 (m, 2H) 1.36 (s, 11H), 0.95 (d, J = 6.4 Hz, 3H), 0.81-0.73 (m, 1H); HPLC (method 4) 94.9% (area under the curve), t _R = 6.83 minutes; ESI + APCI-MS m / z 598 [M + H] ⁺ .

N- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl Group) Preparation of cyclohexylamine 2-6c (Example 2-114)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a In the same method, 3- (aminomethyl) pyrrolidine-1-carboxylic acid tert-butyl ester 2-5c is used to prepare N- (1- (1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) cyclohexylamine 2- 6c and obtained as an off-white solid (52% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.02 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.68 (s, 1H), 6.65 (dd, J = 2.4, 7.6Hz, 1H), 6.56 (d, J = 1.6Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.79 (d, J = 12Hz, 2H), 2.79-2.57 ( m, 4H), 1.91-1.67 (m, 6H), 1.58-1.51 (m, 2H), 1.40-1.13 (m, 7H), 1.17-1.13 (m, 3H); HPLC (Method 4) 98.1% (curve Lower area), t _R = 6.73 minutes; ESI + APCI-MS m / z 497 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 2-cyclohexylethyl) ethyl-1-amine 2-6d (Example 2-84)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a, using the same method, 2-cyclohexylethan-1-amine 2-5d to prepare 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (2- cyclohexylethyl) acetate 1-Amine 2-6d and obtained as an off-white solid (yield 40%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.03 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.86 (s, 1H), 6.68 (d, J = 2.8, Hz, 1H) , 6.66 (d, J = 2.0, Hz, 1H), 6.57 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.80 (d, J = 12.0Hz, 2H), 2.71-2.60 (m, 3H), 2.56-2.48 (m, 2H), 1.72-1.56 (m, 8H), 1.39-1.16 (m, 8H), 0.98 (d, J = 6.4Hz, 3H), 0.90-0.80 (m , 2H); HPLC (Method 4) 98.6% (area under the curve), t _R = 6.95 minutes; ESI + APCI-MS m / z 525 [M + H] ⁺ .

4-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Ethyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester ( tert -butyl 4-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ Preparation of 1,2- a ] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) piperidine-1-carboxylate) 2-6e (Example 2-105)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N - (cyclopentylmethyl) ethan-l-amine in the same manner 2-6a, using 4- (aminomethyl) piperidine-1-carboxylate (tert -butyl 4- (aminomethyl) piperidine- 1-carboxylate) 2-5e Preparation of 4-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Methyl) piperidine-4-yl) ethyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 2-6e and obtained as an off-white solid (yield 32%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.01 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.68 (s, 1H), 6.65 (dd, J = 2.4, 7.6Hz, 1H), 6.56 (s, 1H), 3.98 (d, J = 13.2Hz, 2H), 3.92 (s, 3H), 3.84 (s, 3H), 3.78 (d, J = 12.0Hz , 2H), 2.68-2.63 (m, 4H), 2.47-2.43 (m, 2H), 2.38-2.33 (m, 1H), 1.75-1.64 (m, 4H), 1.59-1.48 (m, 2H), 1.35 (s, 11H), 1.03-0.99 (m, 2H), 0.96 (d, J = 6.4 Hz, 3H); HPLC (method 10) 98.9% (area under the curve), t _R = 6.85 minutes; ESI + APCI- MS m / z 612 [M + H] ⁺ .

4- (3-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) ethyl) amino) propyl) piperidine-1-carboxylic acid tert-butyl tert -butyl 4- (3-((1- (1- (2- (5-chloro-2,4- dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) propyl) piperidine-1-carboxylate) 2-6f (Example 2-103)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a. 4- (3-Aminopropyl) piperidine-1-carboxylic acid tert-butyl ester 2-5f was used to prepare 4- (3- ((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl ) Amino) propyl) piperidine-1-carboxylic acid tert-butyl ester 2-6f and obtained as an off-white solid (32% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.02 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.69 (s, 1H), 6.66 (dd, J = 2.4, 7.6Hz, 1H), 6.56 (s, 1H), 3.97 (s, 3H), 3.92 (br s, 2H), 3.85 (s, 3H) 3.79 (d, J = 11.6Hz, 2H), 2.70 -2.43 (m, 7H), 1.72-1.44 (m, 8H), 1.42-1.34 (m, 11H), 1.22-1.16 (m, 2H), 0.97 (d, J = 6.4Hz, 5H); HPLC (method 4) 92.3% (area under the curve), t _R = 6.96 minutes; ESI + APCI-MS m / z 640 [M + H] ⁺ .

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Preparation of 2-6 g of ethyl-1-amine (Example 2-97)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a, N -benzyl-1- (1- (2- (5-chloro-2, 4-Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl-1-amine 2-6 g, and obtained as an off-white solid (yield 28%) ).

¹ H NMR (400MHz, CD ₃ OD): δ 8.00 (d, J = 7.6Hz, 1H), 7.96 (s, 1H), 7.84 (s, 1H), 7.27-7.13 (m, 5H), 6.67 (s , 1H), 6.64 (dd, J = 2.4,7.6Hz, 1H), 6.54 (d, J = 2.0Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.76 (m, J = 12.8Hz, 3H), 3.63 (d, J = 13.2Hz, 1H), 2.67-2.61 (m, 2H), 2.49-2.46 (m, 1H), 1.70 (d, J = 12.4Hz, 2H), 1.53- 1.47 (m, 1H), 1.36-1.27 (m, 2H), 0.98 (d, J = 6.4 Hz, 3H); HPLC (method 4) 98.1% (area under the curve), t _R = 6.73 minutes; ESI + APCI -MS m / z 497 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -benzene Preparation of ethyl ethyl-1-amine 2-6h (Example 2-115)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a The same method, using 2-phenylethyl-1-amine 2-5h to prepare 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -phenethylethyl-1-amine 2-6h, and obtained as an off-white solid (41% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 7.99 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.83 (s, 1H), 7.21-7.08 (m, 5H), 6.66 (s , 1H), 6.62 (dd, J = 2.4,7.6Hz, 1H), 6.53 (s, 1H), 3.90 (s, 3H), 3.83 (s, 3H), 3.72 (m, 2H), 2.84-2.80 ( m, 1H), 2.73-2.57 (m, 5H), 2.49-2.42 (m, 1H), 1.64-1.42 (m, 3H), 1.30-1.12 (m, 2H), 0.97 (d, J = 6.4Hz, 3H); HPLC (method 9) 98.2% (area under the curve), t _R = 7.40 minutes; ESI + APCI-MS m / z 519 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 2-cyclopentylethyl) ethyl-1-amine 2-6i (Example 2-116)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a The same method, using 2-cyclopentylethyl-1-amine 2-5i to prepare 1- (1- (2- (5-chloro-2, 3,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (2- cyclopentylethyl) ethan-1-amine 2- 6i and obtained as an off-white solid (38% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.01 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.68 (s, 1H), 6.65 (dd, J = 2.4, 7.6Hz, 1H), 6.56 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.77 (d, J = 12.8Hz, 2H), 2.70-2.49 (m, 5H) , 1.72-1.69 (m, 5H), 1.57-1.35 (m, 9H), 1.10-1.03 (m, 2H), 0.99 (d, J = 6.4Hz, 3H); HPLC (method 5) 98.3% (under the curve Area), t _R = 6.85 minutes; ESI + APCI-MS m / z 511 [M + H] ⁺ .

3-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Ethyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester ( tert -butyl 3-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ Preparation of 1,2- a ] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) piperidine-1-carboxylate) 2-6j (Example 2-117)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a The same method was used to prepare 3-((((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) Methyl) piperidine-1-carboxylic acid tert-butyl ester 2-6j and obtained as an off-white solid (47% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.01 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.68 (s, 1H), 6.65 (dd, J = 2.0, 7.6Hz, 1H), 6.55 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.77 (d, J = 12.8Hz, 3H), 2.69-2.56 (m, 3H) , 2.48-2.33 (m, 3H), 1.78-1.70 (m, 3H), 1.58-1.51 (m, 3H), 1.36 (s, 11H), 1.18-1.11 (m, 4H), 0.95 (d, J = 6.4 Hz, 3H); HPLC (Method 5) 99.5% (area under the curve), t _R = 6.89 minutes; ESI + APCI-MS m / z 612 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of cyclohexylmethyl) ethyl-1-amine 2-6k (Example 2-118)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Cyclopentylmethyl) ethyl-1-amine 2-6a The same method was used to prepare 1- (1- (2- (5-chloro-2,4-dimethoxy) using cyclohexylmethylamine 2-5k phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (cyclohexylmethyl) ethan-l-amine 2-6k, and to obtain an off-white solid (yield Rate 32%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.00 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.84 (s, 1H), 6.67 (s, 1H), 6.64 (dd, J = 2.0, 7.6Hz, 1H), 6.54 (brs, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.77 (d, J = 12.8Hz, 2H), 2.67-2.61 (m, 2H) , 2.45-2.37 (m, 2H), 2.31-2.27 (m, 1H), 1.70-1.58 (m, 7H), 1.38-1.15 (m, 7H), 0.95 (d, J = 6.4Hz, 3H), 0.85 -0.82 (m, 2H); HPLC (method 4) 98.7% (area under the curve), t _R = 6.81 minutes; ESI + APCI-MS m / z 511 [M + H] ⁺ .

Option 8

2- (1- (2-Aminopyridin-4-yl) pyrrolidin-3-yl) acetate (methyl 2- (1- (2-aminopyridin-4-yl) pyrrolidin-3-yl) acetate) Preparation of 3-2

To a suspension of 4-chloropyridine-2-amine (20 mg, 0.156 mmol) in N , N' -diisopropylethylamine (2.0 mL) was added 2- (1- (2-aminopyridine-4- (Methyl) pyrrolidin-3-yl) methyl acetate hydrochloride (methyl 2- (1- (2-aminopyridin-4-yl) pyrrolidin-3-yl) acetate hydrochloride) (30 mg, 0.171 mmol), and at 120 The reaction mixture was heated at 16 ° C for 16 hours. The reaction mixture was cooled to room temperature, and the N, N '- diisopropylethylamine decantation (, Decant), and the residue was 15% [(5% NH ₃ in CH ₃ OH) and CH ₂ Cl ₂ ))] and saturated NaHCO ₃ aqueous solution (10 mL: 5 mL). The layers were separated, and the organic layer was washed with brine (2.0 mL), dried over anhydrous Na ₂ SO ₄ , filtered, and concentrated under reduced pressure. The residue was triturated with hexane and dried to give methyl 2- (1- (2-aminopyridin-4-yl) pyrrolidin-3-yl) acetate 3-2 (20 mg, raw) as a brown solid It was used directly in the next step without further purification.

2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) acetic acid methyl ester ( Preparation of methyl 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) acetate) 3-3

At 75 ° C, 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 3-1 (0.80 g, 2.73 mmol) and 2- ( A mixture of methyl 1- (2-aminopyridin-4-yl) pyrrolidin-3-yl) acetate 3-2 (0.63 g, 2.73 mmol) was heated for 16 hours. The reaction mixture was cooled to room temperature, and the formed precipitate was collected by filtration, washed with hexane (20 mL), and dried. With stirring at ambient temperature for 1 hour, using aqueous NaHCO ₃ (15.0 mL) hydrobromide salinization. The solid was collected by filtration, washed with water and dried to give 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Methyl) pyrrolidin-3-yl) acetate 3-3 (0.45 g, 41%) as an off-white solid. ESI + APCI-MS m / z 430 [M + H] ⁺ .

2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) acetic acid (2- Preparation of (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) acetic acid) 3-4

For 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a in THF, CH ₃ OH and water (10 mL / 10 mL / 2 mL) ] Pyridine-7-yl) pyrrolidin-3-yl) methyl acetate 3-3 (0.5 g, 1.16 mmol) solution, LiOH‧H ₂ O (0.14 g, 3.49 mmol) was added, and the resulting product was stirred at ambient temperature The mixture was for 5 hours. The solvent was evaporated and the residue was diluted with water and extracted with ethyl acetate (2 × 10 mL). The aqueous layer was adjusted to pH 3 to 4 with a 10% KHSO ₄ aqueous solution. The formed precipitate was collected by filtration, washed with water and dried to give 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) pyrrolidin-3-yl) acetic acid 3-4 (270 mg, raw) as an off-white solid, which was used in the next step without further purification. ESI + APCI MS m / z 416 [M + H] ⁺ .

2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -methyl Oxy- N -methylacetamide (2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) -N -methoxy- N -methylacetamide) 3-5

For 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine in DMF (5.0 mL) -3-yl) acetic acid 3-4 (0.25 g, 0.602 mmol), N , O -dimethylhydroxylamine hydrochloride (116 mg, 1.20 mmol) and N , N' -diisopropylethylamine (466 mg, 3.61 mmol) solution, EDC‧HCl (345 mg, 1.80 mmol) and HOBt (243 mg, 1.80 mmol) were added. The resulting mixture was stirred at ambient temperature for 15 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (2 x 10 mL). The combined organic layers were dried over anhydrous Na ₂ SO ₄ , filtered and concentrated to give 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) pyrrolidin-3-yl) -N -methoxy- N -methylacetamidine 3-5 (200 mg, raw). The crude compound was used directly in the next step without further purification. ESI + APCI MS m / z 459 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) propan-2- Ketone (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) propan-2-one) 3-6 Preparation

For 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine in THF (10 mL)- 3-yl) -N -methoxy- N -methylacetamide 3-5 (0.2 g, 0.436 mmol) solution, CH ₃ MgBr solution (3M, 0.43 mL, 1.31 mmol) in ether was added at ambient temperature. ). The reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was cooled to 0 ℃ and treated with an aqueous solution of ₄ Cl NH quenched. The aqueous layer was extracted with ethyl acetate (2 × 20 mL). The combined organic layers were dried over anhydrous Na ₂ SO ₄ , filtered and concentrated to give 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) pyrrolidin-3-yl) propan-2-one 3-6 (160 mg, raw), which was used directly in the next step without further purification. ESI + APCI MS m / z 414 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-ethylpiperidin-4-yl) methyl) propan-2-amine 3-8 (Example 2-119)

For 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) in CH ₃ OH (5.0 mL) A suspension of pyrrolidin-3-yl) propan-2-one 3-6 (100 mg, 0.242 mmol) and (1-ethylpiperidin-4-yl) methylamine 3-7 (51 mg, 0.3631 mmol) was added to acetic acid (0.05 mL), and the reaction mixture was stirred at 80 ° C for 12 hours. Sodium cyanoborohydride (45 mg, 0.72 mmol) was added in one portion, and the reaction mixture was stirred at the same temperature for another 6 hours. The reaction mixture was cooled to ambient temperature, diluted with aqueous sodium bicarbonate solution, and extracted with CH ₂ Cl ₂ (2 × 10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by combination-rapid concomitant (silicone, NH ₄ OH / CH ₃ OH / CH ₂ Cl ₂ , 1: 9: 90) yields 1- (1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -((1-ethylpiperidin-4-yl) methyl) propane- 2-amine 3-8 (20 mg, 15%) as an off-white solid.

¹ H NMR (400MHz, CD ₃ OD) δ: 7.99 (d, J = 7.6Hz, 1H), 7.96 (s, 1H), 7.79 (s, 1H), 6.68 (s, 1H), 6.41 (dd, J = 2.0, 7.2Hz, 1H), 6.15 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.50 (q, J = 9.2Hz, 1H), 3.39-3.34 (m, 1H) , 3.30 (q, J = 8.8Hz, 1H), 2.91 (d, J = 9.6Hz, 3H), 2.68-2.60 (m, 1H), 2.49-2.30 (m, 5H), 2.17-2.09 (m, 1H ), 1.92-1.86 (m, 2H), 1.72 (q, J = 12.8Hz, 2H), 1.65-1.57 (m, 2H), 1.46-1.37 (m, 2H), 1.23-1.18 (m, 1H), 1.16-1.12 (m, 1H), 1.06 (q, J = 4.0Hz, 3H), 1.02 (dt, J = 1.6, 7.2Hz, 3H); HPLC (method 4) 94.8% (area under the curve), t _R = 6.38 minutes; ESI + APCI MS m / z 540 [M + H] ⁺ .

Option 9

Preparation of 1- (2-aminopyridin-4-yl) piperidine-4-carboxylic acid ethyl ester 4-3

Of the N, N '- diisopropylethylamine (N, N' -diisopropylethyl amine) 4- chloro-pyridine (25mL) -2- amine 4-1 (2.00g, 15.6mmol) was added piperidine Ethyl-4-carboxylate 4-2 (3.67 g, 23.4 mmol). The reaction mixture was heated in a sealed tube at 110 ° C for 16 hours. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure, allowing the residue to be distinguished between EtOAc and water (200 mL / 50 mL). The layers were separated, and the EtOAc layer was washed with brine (50 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated. The crude material was triturated with hexane, filtered and dried to give 1- (2-aminopyridin-4-yl) piperidine-4-carboxylic acid ethyl ester 4-3 (2.5 g, 85%) as an off-white solid. ESI + APCI-MS m / z 250 [M + H] ⁺ .

Preparation of 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4-carboxylic acid ethyl ester 4-5

1- (2-Aminopyridin-4-yl) piperidine-4-carboxylic acid ethyl ester 4-3 (2.5 g, 10.0 mmol) and 2-bromo-1 in acetone (120 mL) at 75 ° C. A mixture of-(5-chloro-2,4-dimethoxyphenyl) ethanone 4-4 (3.2 g, 11.0 mmol) was heated for 16 hours. The reaction mixture was cooled to room temperature, and the white precipitate formed was collected by filtration, washed with hexane (200 mL) and dried. The crude product was suspended in water (200 mL) and a saturated aqueous NaHCO ₃ solution (200 mL), and stirred at room temperature for 1 hour. The resulting solid was collected by filtration, washed with water and dried to give ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Propyl) piperidin-4-yl) methyl) t-butylaminocarbamate 4-5 (1.2 g, 43%) as an off-white solid.

¹ H NMR (400MHz, CDCl ₃ ): δ 8.37 (s, 1H), 7.89-7.86 (m, 2H), 6.81 (s, 1H), 6.58 (s, 1H), 6.55 (dd, J = 2.4,7.6 Hz, 1H), 4.16 (q, J = 7.2Hz, 2H), 3.99 (s, 3H), 3.95 (s, 3H), 3.71-3.67 (m, 2H), 2.90-2.83 (m, 2H), 2.52 -2.46 (m, 1H), 2.06-2.03 (m, 2H), 1.92-1.83 (m, 2H), 1.27 (t, J = 7.2Hz, 3H); ESI + APCI MS m / z 444 [M + H ] ⁺ .

Preparation of 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4-carboxaldehyde 4-6

For 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 in CH ₂ Cl ₂ (50 mL) cooled to -78 ° C -Yl) piperidine-4-carboxylic acid ethyl ester 4-5 (500 mg, 1.1 mmol), and DIBAL-H (1.1 mL, 1.6 mmol) was added dropwise. The resulting mixture was stirred at -78 ° C for 1 hour. The reaction mixture was quenched with saturated aq. NH ₄ Cl and extracted with CH ₂ Cl ₂ (2 × 50 mL). The combined organic extracts were dried over anhydrous Na ₂ SO ₄ , filtered and concentrated under reduced pressure to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) piperidine-4-carbaldehyde 4-6 (300 mg, 76%) as an off-white solid. ESI + APCI-MS m / z 400 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of thien-2-ylmethyl) methylamine 4-8a (Example 2-2)

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 in CH ₃ OH (5 mL) -A suspension of formaldehyde 4-6 (80 mg, 0.20 mmol) and thiophen-2-ylmethanamine 4-7a (44 mg, 0.30 mmol), acetic acid (0.1 mL) was added, and the resulting mixture was stirred 2 hours. Sodium cyanoborohydride (62 mg, 1.00 mmol) was added, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous NaHCO ₃ and extracted with CH ₂ Cl ₂ (2 × 20 mL). Dried over anhydrous Na ₂ SO ₄ the combined organic extracts were dried, filtered and concentrated. The crude material was purified by combinatorial-fast chromatography [silica gel; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to obtain 1- (1- (2- (5-chloro 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (thiophen-2-yl) methylamine 4- 8a (18 mg, 19%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.36 (t, J = 3.6Hz, 1H) , 6.94 (d, J = 3.6Hz, 2H), 6.86 (s, 1H), 6.78 (dd , J = 2.4, 7.6Hz, 1H), 6.62 (d, J = 1.6Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.88 (s, 2H), 3.77 (d, J = 12.4Hz, 2H), 2.74-2.66 (m, 2H), 2.44 (d, J = 6.4Hz, 2H), 1.81 (d, J = 11.6Hz, 2H), 1.61-1.58 (m, 1H), 1.27-1.17 (m, 2H); HPLC (Method 13) 97.7% (area under the curve), t _R = 6.59 minutes; ESI + APCI MS m / z 497 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 2-cyclopentylethyl-1-amine 4-8b (Example 2-37)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a, N -((1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2-cyclopentylethyl-1-amine 4-8b, and Obtained as an off-white solid (70% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.4,7.6Hz, 1H), 6.64 (d, J = 1.6Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.79 (d, J = 12.4Hz, 2H), 2.74- 2.67 (m, 2H), 2.63-2.59 (m, 2H), 2.55-2.52 (m, 2H), 1.82-1.66 (m, 6H), 1.58-1.53 (m, 2H), 1.51-1.43 (m, 4H ), 1.28-1.20 (m, 2H), 1.09-1.02 (m, 2H); HPLC (method 12) 99.6% (area under the curve), t _R = 6.81 minutes; ESI + APCI-MS m / z 497 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 4-methylcyclohex-1-amine 4-8c (Example 2-66)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a Using the same method as 4-methylcyclohex-1-amine 4-7c to prepare N -((1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -4-methylcyclohex-1-amine 4-8c, and Obtained as an off-white solid (21% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.76 (d, J = 7.6Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 11.6Hz, 2H), 2.73-2.67 (m, 2H), 2.59-2.58 (m, 2H), 2.43 (s, 1H), 1.84-1.81 (m, 3H), 1.65-1.45 (m, 5H), 1.34-1.21 (m, 5H), 1.03-0.91 (m, 1H ), 0.88-0.84 (m, 3H); HPLC (Method 9) 96.1% (area under the curve), t _R = 6.85 minutes; ESI + APCI MS m / z 497 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 4-ethylcyclohex-1-amine 4-8d (Example 2-73)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a Using the same method, 4-ethylcyclohex-1-amine 4-7d was used to prepare N -((1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -4-ethylcyclohex-1-amine 4-8d, and Obtained as an off-white solid (21% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.04 (d, J = 7.2Hz, 1H), 7.96 (s, 1H), 7.87 (s, 1H), 6.69-6.66 (m, 2H), 6.71 (d , J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.78 (d, J = 12.8Hz, 2H), 2.93-2.91 (m, 1H), 2.78-2.71 (m, 4H), 1.83-1.70 (m, 5H), 1.54-1.51 (m, 7H), 1.32-1.27 (m, 4H), 0.84 (t, J = 7.2Hz, 3H); HPLC (method 12) 94.3% ( Area under the curve), t _R = 6.83 minutes; ESI + APCI MS m / z 511 [M + H] ⁺ .

1- (tert-butyl) -N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) piper Preparation of pyridin-4-yl) methyl) piperidine-4-amine 4-8e (Examples 2-29)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a, 1- (tert-butyl) -N -((1 -(2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) piperidine-4 -Amine 4-8e and obtained as an off-white solid (19% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.01 (d, J = 8.4Hz, 1H), 7.97 (s, 1H), 7.84 (s, 1H), 6.68 (s, 1H), 6.64 (dd, J = 2.4, 7.6Hz, 1H), 6.56 (d, J = 2.0Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.73 (d, J = 12.4Hz, 2H), 3.01 (d , J = 12.0Hz, 2H), 2.72-2.67 (m, 2H), 2.43 (d, J = 6.8Hz, 2H), 2.39-2.33 (m, 1H), 2.20 (t, J = 11.6Hz, 2H) , 1.87-1.76 (m, 4H), 1.61-1.56 (m, 1H), 1.37-1.14 (m, 4H), 1.03 (s, 9H); HPLC (method 9) 98.8% (area under the curve), t _R = 6.42 minutes; ESI + APCI MS m / z 540 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of (1-methylpyrrolidin-3-yl) methyl) methylamine 4-8f (Example 2-46)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a The same method was used to prepare 1- (1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -((1-methylpyrrolidin-3-yl) methyl Methyl) methylamine 4-8f and obtained as an off-white solid (22% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.20 (d, J = 7.6 Hz, 1H), 8.00 (d, J = 4.4 Hz, 2H), 6.88 (dd, J = 2.4, 5.2 Hz, 1H), 6.83 (s, 1H), 6.71 (d, J = 2.0Hz, 1H), 4.05 (s, 3H), 3.98 (s, 3H), 3.95 (br s, 2H), 3.16-3.12 (m, 1H), 3.02-2.97 (m, 2H), 2.94-2.89 (m, 3H), 2.80-2.71 (m, 3H), 2.66-2.59 (m, 4H), 2.28-2.19 (m, 1H), 1.95-1.88 (m , 3H), 1.77-1.68 (m, 1H), 1.47-1.30 (m, 3H); HPLC (method 9) 94.8% (area under the curve), t _R = 6.35 minutes; ESI + APCI MS m / z 498 [ M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of (1-ethylpiperidin-3-yl) methyl) methylamine 4-8 g (Example 2-47)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a The same method was used to prepare 1- (1- (2- (5-chloro) using 4-7g of (1-ethylpiperidin-3-yl) methylamine -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -((1-ethylpiperidin-3-yl) 4-8 g of methyl) methylamine was obtained as an off-white solid (yield 28%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.15 (d, J = 7.6Hz, 1H), 8.08 (s, 1H), 7.98 (s, 1H), 6.80 (dd, J = 3.2,2.4Hz, 2H ), 6.70 (d, J = 2.0Hz, 1H), 4.04 (s, 3H), 3.97 (s, 3H), 3.92 (d, J = 12.4Hz, 2H), 3.13 (d, J = 12.0Hz, 1H ), 3.02 (d, J = 12.0Hz, 1H), 2.86-2.81 (m, 2H), 2.60-2.56 (m, 5H), 2.10-1.9.98 (m, 1H), 1.93-1.77 (m, 7H), 1.70-1.63 (m, 1H), 1.43-1.30 (m, 3H), 1.18 (t, J = 7.2Hz, 3H), 1.04-0.98 (m, 1H); HPLC (method 9) 97.4% (area under the curve ), T _R = 6.37 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of (1-ethylpiperidin-4-yl) methyl) methylamine 4-8h (Examples 2-30)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a, using the same method (1-ethylpiperidin-4-yl) methylamine 4-7h to prepare 1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -((1-ethylpiperidin-4-yl) Methyl) methylamine 4-8h and obtained as an off-white solid (yield 35%).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.0, 7.6 Hz, 1H), 6.64 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.80 (d, J = 12.0 Hz, 2H), 2.90 (s, 2H), 2.74-2.66 (m, 2H), 2.63-2.55 (m, 3H), 2.47-2.39 (m, 2H), 2.08-1.73 (m, 5H), 1.70 (d, J = 12.8Hz, 3H), 1.52- 1.44 (m, 1H), 1.28-1.13 (m, 4H), 1.01 (t, J = 6.8 Hz, 3H); HPLC (method 12) 95.3% (area under the curve), t _R = 6.22 minutes; ESI + APCI MS m / z 526 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 2- (1-ethylpiperidine-pyridin-4-yl) ethyl-1-amine 4-8i (Example 2-31)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a Using the same method as 2- (1-ethylpiperidin-4-yl) ethyl-1-amine 4-7i to prepare N -((1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (1-ethyl Piperidine-pyridin-4-yl) ethyl-1-amine 4-8i and obtained as an off-white solid (35% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.17 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.86 (s, 1H), 6.65 (dd, J = 2.4, 7.6Hz, 1H), 6.56 (d, J = 1.6Hz, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.74 (d, J = 12.8Hz, 2H), 2.86 (d , J = 11.6Hz, 2H), 2.73-2.67 (m, 2H), 2.55 (t, J = 8.0Hz, 2H), 2.43 (d, J = 6.8Hz, 2H), 2.35-2.29 (m, 2H) , 1.90 (t, J = 10.4Hz, 2H), 1.77 (d, J = 11.6Hz, 2H), 1.63 (d, J = 11.2Hz, 3H), 1.42-1.36 (m, 2H), 1.29-1.13 ( m, 5H), 1.01 (t, J = 7.2 Hz, 3H); HPLC (method 12) 93.3% (area under the curve), t _R = 6.23 minutes; ESI + APCI MS m / z 540 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 2- (1-propylpiperidin-4-yl) ethyl-1-amine 4-8j (Example 2-51)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a Using the same method as 2- (1-propylpiperidin-4-yl) ethyl-1-amine 4-7j to prepare N -((1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (1-propane Piperidin-4-yl) ethyl-1-amine 4-8j and obtained as an off-white solid (13% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.01 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.86 (s, 1H), 6.65 (dd, J = 2.0,7.6Hz, 1H), 6.56 (d, J = 2.0Hz, 1H), 3.92 (s, 3H), 3.84 (s, 3H), 3.74 (d, J = 12.8Hz, 2H), 2.85 (d , J = 12.0Hz, 2H), 2.72-2.67 (m, 2H), 2.54 (t, J = 7.6Hz, 2H), 2.42 (d, J = 6.8Hz, 2H), 2.22-2.18 (m, 2H) , 1.90 (t, J = 10.4Hz, 2H), 1.77 (d, J = 12.4Hz, 2H), 1.62 (d, J = 11.2Hz, 2H), 1.46-1.36 (m, 4H), 1.29-1.15 ( m, 6H), 0.83 (t, J = 7.2 Hz, 3H); HPLC (method 9) 98.6% (area under the curve), t _R = 6.45 minutes; ESI + APCI MS m / z 554 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 2- (4-methoxycyclohexyl) ethyl-1-amine 4-8k (Example 2-75)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a. Using the same method, 2- (4-methoxycyclohexyl) ethyl-1-amine 4-7k was used to prepare N -((1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (4-methoxy ring Hexyl) ethyl-1-amine 4-8k and obtained as an off-white solid (18% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.05 (d, J = 7.6Hz, 1H), 7.96 (s, 1H), 7.87 (s, 1H), 6.70-6.67 (m, 2H), 6.58 (d , J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.78 (d, J = 12.4Hz, 2H), 3.38-3.26 (m, 1H), 3.24 (s, 3H) , 2.84-2.70 (m, 6H), 1.81-1.72 (m, 5H), 1.50-1.18 (m, 10H), 1.12-0.92 (m, 1H); HPLC (method 12) 98.2% (area under the curve), t _R = 6.71 minutes; ESI + APCI MS m / z 541 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) Preparation of 2- (cyclohex-1-en-1-yl) ethyl-1-amine 4-8l (Example 2-90)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a, using the same method as 2- (cyclohex-1-en-1-yl) ethyl-1-amine 4-7l to prepare N -((1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (cyclohexyl- 1-en-1-yl) ethyl-1-amine 4-8l and obtained as an off-white solid (yield 14%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (d, J = 7.6Hz, 1H), 6.63 (s, 1H), 5.39 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.4Hz, 2H), 2.74 2.67 (m, 2H), 2.61-2.58 (m, 2H), 2.05-1.93 (m, 2H), 1.89-1.79 (m, 4H), 1.78-1.72 (m, 2H), 1.56-1.48 (m, 6H ), 1.23-1.20 (m, 3H); HPLC (method 9) 98.7% (area under the curve), t _R = 6.86 minutes; ESI + APCI MS m / z 509 [M + H] ⁺ .

4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Preparation of methyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester 4-8m (Example 2-5)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(Thien-2-ylmethyl) methylamine 4-8a The same method was used to prepare 4- (2- (4- (2-aminoethyl) piperidine-1-carboxylic acid tert-butyl ester 4-7m ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino ) Ethyl) piperidine-1-carboxylic acid tert-butyl ester 4-8m, and obtained as an off-white solid (yield 18%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.03 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.86 (s, 1H), 6.67 (dd, J = 5.2, 8.0Hz, 2H ), 6.57 (s, 1H), 3.98 (d, J = 8.4Hz, 2H), 3.92 (s, 3H), 3.85 (s, 3H), 3.76 (d, J = 12.8Hz, 2H), 2.74-2.59 (m, 6H), 2.48 (d, J = 6.8Hz, 2H), 1.79 (d, J = 12.8Hz, 2H), 1.60 (d, J = 12.8Hz, 3H), 1.43-1.39 (m, 2H) , 1.35 (s, 9H), 1.28-1.21 (m, 3H), 1.03-0.98 (m, 2H); HPLC (method 9) 98.7% (area under the curve), t _R = 6.99 minutes; ESI + APCI MS m / z 612 [M + H] ⁺ .

Option 10

Preparation of 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylic acid methyl ester 5-2

To a solution of 4-chloropyridine-2-amine 5-1 (0.48 g, 3.75 mmol) in N , N' -diisopropylethylamine (10 mL), methylpyrrolidine-3-carboxylic acid hydrochloric acid was added Methyl pyrrolidine-3-carboxylate hydrochloride salt (0.93 g, 5.65 mmol). The reaction mixture was heated in a sealed tube at 120 ° C for 16 hours. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was partitioned between EtOAc and saturated aqueous NaHCO _3: distinguishing between (300mL 100mL). The layers were separated, and the organic layer was washed with brine (10 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated. The residue was triturated with hexane and dried to give 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylic acid methyl ester 5-2 (700 mg, unprocessed) as an off-white solid, which was directly It was used in the next step without further purification. ESI + APCI-MS m / z 222 [M + H] ⁺ .

Preparation of 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid methyl ester 5-4

At 75 ° C, 1- (2-aminopyridin-4-yl) pyrrolidine-3-carboxylic acid methyl ester 5-2 (0.50 g, 2.262 mmol) and 2-bromo-1 in acetone (50 mL) were added. A mixture of-(5-chloro-2,4-dimethoxyphenyl) ethanone 5-3 (0.726 g, 2.48 mmol) was heated for 16 hours. The reaction mixture was cooled to room temperature, and the white precipitate formed was collected by filtration, washed with hexane (20 mL), and dried. With stirring at room temperature for 1 hour, treated with saturated NaHCO ₃ aqueous solution (5.0 mL) hydrobromide salinization. The solid was collected by filtration, washed with water and dried to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) pyrrole Methane-3-carboxylic acid methyl ester 5-4 (0.2 g, 47%) as an off-white solid.

¹ H NMR (400MHz, CDCl ₃ ): δ 8.31 (s, 1H), 7.80 (d, J = 7.2Hz, 1H), 7.74 (s, 1H), 6.50 (s, 1H), 6.41 (s, 1H) , 6.28 (dd, J = 2.0, 7.2 Hz, 1H), 3.92 (s, 3H), 3.88 (s, 3H), 3.68 (s, 3H), 3.56 (d, J = 7.2Hz, 2H), 3.44- 3.40 (m, 1H), 3.37-3.31 (m, 1H), 3.22-3.15 (m, 1H), 2.29-2.24 (m, 2H). ESI + APCI-MS m / z 416 [M + H] ⁺ .

Preparation of 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid 5-5

For 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- in THF, CH ₃ OH and water (20 mL / 10 mL / 5 mL) 7-yl) pyrrolidine-3-carboxylic acid methyl ester 5-4 (1.0 g, 2.4 mmol) solution, LiOH‧H ₂ O (0.40 g, 9.6 mmol) was added, and the resulting mixture was stirred at ambient temperature for 5 hours . The solvent was evaporated and the residue was diluted with water and extracted with ethyl acetate (2 × 10 mL). The aqueous layer was acidified to pH 3 to 4 with 10% KHSO ₄ solution, and the formed precipitate was collected by filtration, washed with water and dried to give 1- (2- (5-chloro-2,4-dimethoxybenzene) Yl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3-carboxylic acid 5-5 (750 mg, 78%) as an off-white solid.

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.5Hz, 1H), 8.16 (s, 1H), 7.96 (s, 1H), 6.85 (s, 1H), 6.51 (d, J = 6.6Hz, 1H), 6.24 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.57-3.46 (m, 2H), 3.37-3.33 (m, 2H), 3.25-3.18 (m, 1H), 2.27-2.17 (m, 2H); ESI + APCI MS m / z 402 [M + H] ⁺ .

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) -N -methoxy- N -methylpyrrolidine- Preparation of 3-formamidine 5-6

For 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- in DMF (2.0 mL) Carboxylic acid 5-5 (200mg, 0.498mmol), N , O -dimethylhydroxylamine hydrochloride (72mg, 0.747mmol), N , N' -diisopropylethylamine (256mg, 1.99mmol) were mixed and added EDC‧HCl (190 mg, 0.996 mmol) and HOBt (152 mg, 0.996 mmol). The reaction mixture was stirred at ambient temperature for 15 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (2 x 30 mL). The combined organic layers were washed with water and then with brine, dried over anhydrous Na ₂ SO ₄ , filtered and concentrated to give 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) -N -methoxy- N -methylpyrrolidine-3-carboxamide 5-6 (200 mg, raw). The crude material was used in the next step without further purification.

¹ H NMR (300 MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.95 (s, 1H), 6.85 (s, 1H), 6.51 (d, J = 7.5Hz, 1H), 6.23 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.72 (s, 3H), 3.59-3.55 (m, 2H), 3.42-3.37 (m 3H), 3.15 (s, 3H), 2.26-2.08 (m, 2H); ESI + APCI MS m / z 445 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) propan-1- Ketone (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) propan-1-one) 5-7 Preparation

At ambient temperature, 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl)-in THF (500 mL) N -methoxy- N -methylpyrrolidine-3-carboxamide 5-6 (1.0 g, 2.25 mmol) solution, CH ₃ CH ₂ MgBr solution in THF was added) (2.0 M, 3.35 mL, 6.70 mmol). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was quenched with a saturated aqueous solution of NH ₄ Cl at 0 ° C and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried over anhydrous Na ₂ SO ₄ , filtered and concentrated to give 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) pyrrolidin-3-yl) propan-1-one 5-7 (700 mg, raw), which was used directly in the next step without further purification. ESI + APCI MS m / z 414 [M + H] +.

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of (1-ethylpiperidin-4-yl) methyl) propan-1-amine 5-8 (Examples 2-28)

For 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) in CH ₃ OH (5.0 mL) Pyrrolidin-3-yl) propan-1-one 5-7 (100 mg, 0.242 mmol) and (1-ethylpiperidin-4-yl) methylamine (51 mg, 0.36 mmol) were added to acetic acid (0.05 mL), And at 80 ° C, the resulting mixture was stirred for 12 hours. Sodium cyanoborohydride (45 mg, 0.72 mmol) was added, and the reaction mixture was stirred at 80 ° C for another 6 hours. The reaction mixture was cooled to ambient temperature, diluted with aqueous sodium bicarbonate solution, and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined organic layers were dried ₂ SO ₄ dried over anhydrous Na, filtered, and concentrated under reduced pressure. The residue was purified by combination-rapid concomitant (silica gel, NH ₄ OH / CH ₃ OH / CH ₂ Cl ₂ , 1: 9: 90) to obtain 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -((1-ethylpiperidin-4-yl) methyl) propane 1-Amine 5-8 (20 mg, 15%) as an off-white solid.

¹ H NMR (400MHz, CD3OD) δ: 8.00 (d, J = 7.6Hz, 1H), 7.95 (s, 1H), 7.80 (s, 1H), 6.69 (s, 1H), 6.42 (dd, J = 2.4 , 7.6Hz, 1H), 6.16 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.49-3.24 (m, 4H), 3.07-2.91 (m, 3H), 2.50-2.34 ( m, 6H), 2.17-2.04 (m, 1H), 2.01-1.93 (m, 2H), 1.79-1.67 (m, 3H), 1.67-1.50 (m, 1H), 1.44-1.37 (m, 2H), 1.22-1.16 (m, 1H), 1.05 (t, J = 6.8Hz, 3H), 0.90 (t, J = 7.2Hz, 3H); HPLC (method 4) 93.6% (area under the curve), t _R = 6.35 Minutes; ESI + APCI MS m / z 540 [M + H] ⁺ .

Option 11

Preparation of ((1- (2-aminopyridin-4-yl) piperidin-4-yl) methyl) t-butylaminoformate 6-3

To a solution of 4-chloropyridine-2-amine 6-1 (2.50 g, 19.5 mmol) in a mixture of isopropanol and N , N' -diisopropylethylamine (50 mL / 25 mL), (piperidine- Tert-Butyl 4-ylmethyl) carbamate 6-2 (6.30 g, 29.4 mmol). The reaction mixture was heated in a sealed tube at 120 ° C for 24 hours. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc and differentiate saturated aqueous NaHCO ₃ (300mL / 100mL). The layers were separated, the EtOAc layer was washed with brine (100 mL), dried over Na ₂ SO _4, filtered and concentrated. The residue was triturated with hexane, filtered and dried to give ((1- (2-aminopyridin-4-yl) piperidin-4-yl) methyl) aminocarboxylic acid tert-butyl 6-3 (5.50 g , 92%) as a white solid, which was used directly in the next step without further purification. ESI + APCI-MS m / z 307 [M + H] ⁺ .

((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino Preparation of tert-butyl formate 6-5

Tert-Butyl ((1- (2-aminopyridin-4-yl) piperidin-4-yl) methyl) carbamate 6-3 (5.00g, 16.3 mmol) and a mixture of 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 6-4 (5.30 g, 18.1 mmol) was heated for 16 hours. The reaction mixture was cooled to room temperature. The formed precipitate was collected by filtration, washed with hexane (200 mL), and dried. The hydrobromide was taken up in a saturated sodium bicarbonate solution (200 mL), and stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and dried to give ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) t-butylaminocarbamate 6-5 (7.1 g, 79%) as an off-white solid.

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 13.13 (br s, 1H), 8.49 (d, J = 7.8 Hz, 1H), 8.23 (s, 1H), 7.91 (s, 1H), 7.29 (d , J = 6.0Hz, 1H), 6.98-6.92 (m, 2H), 6.66 (s, 1H), 4.05-3.98 (m, 8H), 3.03 (t, J = 12.6Hz, 2H), 2.85 (t, J = 5.4 Hz, 2H), 1.75 (d, J = 11.7 Hz, 3H), 1.38 (s, 9H), 1.23-1.14 (m, 2H); HPLC (method 9) 99.2% (area under the curve), t _R = 13.78 points; ESI + APCI-MS m / z 501 [M + H] ⁺ .

Preparation of 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methylamine 6-6

((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine in CH ₂ Cl ₂ (30 mL) A suspension of pyridin-4-yl) methyl) carbamic acid tert-butyl 6-5 (3.00 g, 5.98 mmol) was added to a solution of HCl (4.0 M in 1,4-dioxane, 30 mL) and The reaction mixture was stirred at room temperature for 16 hours. The resulting solid was collected by filtration, washed with CH ₂ Cl ₂ (100 mL) and dried. The solid was then suspended in water (70 mL) and basified with a saturated sodium bicarbonate solution (70 mL) by stirring at room temperature for 1 hour. The formed pale yellow solid was collected by filtration, washed with water and dried to give (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) piperidin-4-yl) methylamine 6-6 (2.1 g, 87%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.77 (d, J = 6.0Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.4Hz, 2H), 2.87 (t, J = 2.0Hz, 2H), 2.70 (t, J = 11.6Hz, 2H), 1.74-1.58 (m, 3H), 1.24-1.16 (m, 2H); ESI + APCI-MS m / z 401 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( 2,5-Dimethoxybenzyl) methylamine (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4 -yl) - N - (2,5- dimethoxybenzyl) methanamine) preparation of 6-8a (Example 2-14)

For (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- in CH ₃ OH (5 mL)- 4-yl) methylamine 6-6 (150 mg, 0.37 mmol) and 2,5-dimethoxybenzaldehyde 6-7a (68 mg, 0.41 mmol) suspension, add acetic acid (0.1 mL ), And the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (118 mg, 1.87 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate (20 mL), and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined were washed with brine (20mL) The organic extracts were dried over anhydrous Na ₂ SO _4, filtered and concentrated. The residue was purified by combi-rapid color chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to obtain 1- (1- (2- (5-chloro 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (2,5- dimethoxybenzyl) A Amine 6-8a (70 mg, 39%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.19 (d, J = 8.4Hz, 1H) , 6.86 (s, 1H), 6.77 (dd, J = 2.4, 7.6 Hz, 1H), 6.62 (s, 1H), 6.58 (d, J = 2.4 Hz, 1H), 6.47 (dd, J = 2.0, 7.0 Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.80 (d, J = 10.0Hz, 3H), 3.76 (s, 3H), 3.73 (s, 3H), 3.60 (s, 2H ), 2.74-2.67 (m, 2 H), 2.40 (d, J = 6.4 Hz, 2H), 1.80 (d, J = 12.0 Hz, 2H), 1.66-1.53 (m, 1H), 1.23-1.17 (m 1H); HPLC (method 10) 91.0% (area under the curve), t _R = 6.76 minutes; ESI + APCI-MS m / z 551 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 4-methoxy-2-nitrobenzyl) methylamine 6-8b (Example 2-17)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a. Using the same method, 4-methoxy-2-nitrobenzaldehyde 6-7b was used to prepare 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (4- Methoxy-2-nitrobenzyl) methylamine 6-8b and obtained as an off-white solid (39% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.25 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.98 (s, 1H), 7.59 (d, J = 8.8Hz, 1H) , 7.40 (d, J = 2.8Hz, 1H), 7.25 (dd, J = 2.8, 11.2Hz, 1H), 6.86 (s, 1H), 6.76 (dd, J = 2.0, 7.6Hz, 1H), 6.61 ( s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.85 (s, 2H), 3.82 (s, 3H), 3.74 (d, J = 12.8Hz, 2H), 2.73-2.66 (m , 2 H), 2.44-2.36 (m, 3 H), 1.78 (d, J = 12.0 Hz, 2H), 1.20-1.15 (m, 2H); HPLC (method 10) 95.1% (area under the curve), t _R = 6.76 minutes; ESI + APCI-MS m / z 566 [M + H] ⁺ .

5-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -2-methoxyphenol 6-8c (Example 2-19)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a The same method was used to prepare 5- (3-hydroxy-4-methoxybenzaldehyde) 6-7c (((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amine (Methyl) methyl) -2-methoxyphenol 6-8c and obtained as an off-white solid (yield 40%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.81 (s, 1H), 8.26 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.82 (d, J = 8.0Hz, 1H), 6.79-6.76 (m, 2H), 6.68 (dd, J = 2.0, 8.4Hz , 1H), 6.62 (d, J = 1.6Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.77 (d, J = 12Hz, 2H), 3.72 (s, 3H), 3.33 (s, 2H), 2.73-2.67 (m, 2H), 2.38 ( d, J = 6.4 Hz, 2H), 1.80 (d, J = 12.0 Hz, 2H), 1.60-1.54 (m, 1H), 1.25-1.17 (m, 2H); HPLC (method 10) 97.6% (under the curve Area), t _R = 6.55 minutes; ESI + APCI-MS m / z 537 [M + H] ⁺ .

2-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -5-methoxyphenol 6-8d (Example 2-41)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a The same method was used to prepare 2- (2-hydroxy-4-methoxybenzaldehyde) 6-7d (((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amine Methyl) methyl) -5-methoxyphenol 6-8d and obtained as an off-white solid (yield 45%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.02 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.87 (d, J = 8.8Hz, 1H), 6.68 (m, 1H), 6.65 (dd, J = 2.4,7.6Hz, 1H), 6.55 (d, J = 2.4Hz, 1H), 6.25-6.22 (m, 2H), 3.92 (s, 3H), 3.84 (s, 3H), 3.74 (d, J = 15.6Hz, 4H), 3.62 (s, 3H), 2.73-2.70 (m, 2H), 2.48 (d, J = 6.8Hz, 2H), 1.78 (d, J = 11.6Hz, 2H), 1.70-1.63 (m, 1H), 1.30-1.18 (m, 2H); HPLC (Method 10) 96.1% (area under the curve), t _R = 6.65 minutes; ESI + APCI-MS m / z 537 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -2-methoxy- N , N -dimethylaniline 6-8e (Example 2-59)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a The same method is used, 4- (dimethylamino) -3-methoxybenzaldehyde (4- (dimethylamino) -3-methoxybenzaldehyde ) 6-7e to prepare 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- 4-yl) methyl) amino) methyl) -2-methoxy- N , N -dimethylaniline 6-8e and obtained as an off-white solid (70 mg, yield 33%).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.91 (s, 1H), 6.86 (s, 1H), 6.79-6.77 (m, 3H), 6.62 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 8.8Hz, 2H), 3.62 (s, 2H), 2.73-2.67 (m, 2H), 2.64 (s, 6H), 2.40 (d, J = 6.4Hz, 2H), 1.82 (d, J = 11.2Hz, 2H), 1.61-1.59 (m, 1H), 1.26-1.17 (m, 2H); HPLC (method 9) 98.3% (area under the curve), t _R = 6.41 minutes; ESI + APCI-MS m / z 564 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( Preparation of 4-methoxy-3-methylbenzyl) methylamine 6-8f (Example 2-39)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a. Using the same method, 4-methoxy-3-methylbenzaldehyde 6-8f was used to prepare 1- ( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (4- methyl Oxy-3-methylbenzyl) methylamine 6-8f and obtained as an off-white solid (yield 30%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.10 (d, J = 8.0Hz, 2H) , 6.85 (d, J = 9.2Hz, 2H), 6.77 (dd, J = 2.0,7.6Hz, 1H), 6.62 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.79 (s, 2H), 3.75 (s, 3H), 3.61 (s, 2H), 2.73-2.67 (m, 2H), 2.40 (d, J = 6.4Hz, 2H), 2.12 (s, 3H ), 1.80 (d, J = 11.6 Hz, 2H), 1.62-1.57 (m, 1H), 1.26-1.19 (m, 2H); HPLC (method 9) 99.5% (area under the curve), t _R = 6.89 minutes ; ESI + APCI-MS m / z 535 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -N , N , 2-trimethylaniline 6-8 g (Example 2-58)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a Same method using 4- (dimethylamino) -3-methylbenzaldehyde 6-7g Preparation of 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) methyl) amino) methyl) -N , N , 2-trimethylaniline 6-8 g and obtained as an off-white solid (yield 44%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.08 (d, J = 8.4Hz, 1H) , 6.86 (s, 1H), 6.74 (dd, J = 2.4, 7.6Hz, 1H), 6.62 (d, J = 2.0Hz, 1H), 6.54 (d, J = 2.4Hz, 1H), 6.51-6.48 ( m, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 8.8Hz, 2H), 3.60 (s, 2H), 2.84 (s, 6H), 2.74-2.66 (m , 2H), 2.52-2.48 (m, 2H), 2.26 (s, 3H), 1.81 (d, J = 11.2Hz, 2H), 1.65-1.59 (m, 1H), 1.27-1.19 (m, 2H); HPLC (Method 9) 98.3% (area under the curve), t _R = 6.41 minutes; ESI + APCI-MS m / z 548 [M + H] ⁺ .

2-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -4-methylphenol 6-8h (Example 2-104)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a The same method was used to prepare 2-((2-hydroxy-5-methylbenzaldehyde) 6-7h ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino ) Methyl) -4-methylphenol for 6-8 h and was obtained as an off-white solid (32% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 10.0Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 6.86 (s, 3H), 6.77 (d, J = 2.0, Hz, 1H), 6.63 (s, 1H), 6.57 (d, J = 11.6Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.80 (d, J = 11.6Hz , 4H), 2.75 (t, J = 15.2Hz, 2H), 2.42 (d, J = 8.4Hz, 2H), 2.16 (s, 3H), 1.79 (d, J = 15.2Hz, 2H), 1.65-1.59 (m, 1H), 1.29-1.18 (m, 2H); HPLC (method 9) 99.5% (area under the curve), t _R = 6.69 minutes; ESI + APCI-MS m / z 521 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( Preparation of 2-methoxy-5-methylbenzyl) methylamine 6-8i (Example 2-86)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a. Using the same method, 2-methoxy-5-methylbenzaldehyde 6-7i was used to prepare 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (2- Methoxy-5-methylbenzyl) methylamine 6-8i was obtained as an off-white solid (yield 27%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.01 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.84 (s, 1H), 6.97 (d, J = 8.4Hz, 2H), 6.77 (d, J = 8.0Hz, 1H), 6.86-6.63 (m, 2H), 6.55 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.72 (d, J = 10.0Hz , 5H), 3.65 (s, 2H), 2.72-2.66 (m, 2H), 2.41 (d, J = 6.8Hz, 2H), 2.17 (s, 3H), 1.75 (d, J = 12.8Hz, 2H) , 1.65-1.64 (m, 1H), 1.25-1.17 (m, 2H); HPLC (method 10) 97.3% (area under the curve), t _R = 6.85 minutes; ESI + APCI-MS m / z 536 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( 2,3-dimethylbenzyl) methylamine (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4- yl) - N - (2,3- dimethylbenzyl) methanamine) 6-8j prepared (Examples 2-81)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a, using the same method, to prepare 1- (1- (2 - (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (2,3- dimethyl Benzyl) methylamine 6-8j and obtained as an off-white solid (36% yield).

¹ H NMR (400MHz, CDCl ₃ ): δ 8.36 (d, J = 1.6Hz, 1H), 7.87-7.84 (m, 2H), 7.13 (d, J = 2.4Hz, 1H), 7.07 (d, J = 1.6Hz, 2H), 6.81 (s, 1H), 6.57 (d, J = 6.4Hz, 2H), 3.99 (s, 3H), 3.95 (s, 3H), 3.78 (s, 2H), 3.74 (d, J = 12.8Hz, 2H), 2.81 (t, J = 12.0Hz, 2H), 2.61 (d, J = 6.4Hz, 2H), 2.29 (s, 3H), 2.26 (s, 3H), 1.89 (d, J = 12.4Hz, 2H), 1.60-1.53 (m, 1H), 1.42-1.34 (m, 2H); HPLC (Method 9) 99.5% (area under the curve), t _R = 6.84 minutes; ESI + APCI-MS m / z 519 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 4-fluoro-3-methylbenzyl) methylamine 6-8k (Example 2-78)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a. Using the same method, 4-fluoro-3-methylbenzaldehyde 6-7k was used to prepare 1- (1 - (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (4- fluoro - 3-methylbenzyl) methylamine 6-8k and obtained as an off-white solid (16% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 7.99 (d, J = 7.6Hz, 1H), 7.96 (s, 1H), 7.83 (s, 1H), 7.22-7.18 (m, 1H), 6.83-6.75 (m, 2H), 6.66 (s, 1H), 6.63 (dd, J = 2.4,7.6Hz, 1H), 6.54 (d, J = 2.0Hz, 1H), 3.90 (s, 3H), 3.83 (s, 3H), 3.72 (d, J = 12.4Hz, 2H), 3.64 (s, 2H), 2.72-2.65 (m, 2H), 2.46 (d, J = 6.8Hz, 2H), 2.26 (s, 3H), 1.83-1.77 (m, 2H), 1.67-1.60 (m, 1H) 1.28-1.18 (m, 2H); HPLC (method 10) 95.7% (area under the curve), t _R = 6.77 minutes; ESI + APCI-MS m / z 523 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 2-fluoro-3-methylbenzyl) methylamine 6-8l (Example 2-85)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a The same method was used to prepare 1- (1 using 2-fluoro-3-methylbenzaldehyde 6-7l - (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (2-fluoro - 3-Methylbenzyl) methylamine 6-8l and obtained as an off-white solid (31% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.11-8.05 (m, 2H), 7.94 (br s, 1H), 7.20-7.14 (m, 2H), 7.02 (br s, 1H), 6.77 (br s , 2H), 6.64 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.81 (br s, 4H), 2.81 (t, J = 11.6Hz, 2H), 2.51 (s, 2H ), 2.25 (s, 3H), 1.87 (d, J = 3.2 Hz, 2H), 1.78-1.73 (m, 1H), 1.33-1.30 (m, 2H); HPLC (method 9) 96.3% (area under the curve ), T _R = 6.76 minutes; ESI + APCI-MS m / z 523 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of 2-fluoro-5-methylbenzyl) methylamine 6-8m (Example 2-89)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a. Using the same method, 2-fluoro-5-methylbenzaldehyde 6-7m was used to prepare 1- (1 - (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (2-fluoro - 5-methylbenzyl) methylamine 6-8m and obtained as an off-white solid (42% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.26 (d, J = 6.8Hz, 1H) , 7.05-6.95 (m, 2H), 6.86 (s, 1H), 6.78 (d, J = 7.2Hz, 1H), 6.63 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 (d, J = 12.4Hz, 2H), 3.69 (s, 2H), 2.74 (t, J = 12.0Hz, 2H), 2.42 (d, J = 6.4Hz, 2H), 2.27 (s, 3H), 1.81 (d, J = 12.4Hz, 2H), 1.62-1.58 (m, 1H), 1.26-1.18 (m, 2H); HPLC (Method 9) 96.6% (area under the curve), t _R = 6.76 minutes; ESI + APCI-MS m / z 523 [M + H] ⁺ .

6-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -N , N -dimethylpyridin-3-amine 6-8n (Example 2-67)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a. 6-((((((1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl ) -N , N -dimethylpyridin-3-amine 6-8n and obtained as an off-white solid (24% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 8.02 (d, J = 2.8 Hz, 1H), 7.99 (s, 1H) , 7.21 (d, J = 8.8Hz, 1H), 7.09 (dd, J = 3.2,8.8Hz, 1H), 6.86 (s, 1H), 6.77 (dd, J = 2.4,8.0Hz, 1H), 6.63 ( d, J = 2.4Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.80 (d, J = 9.6Hz, 2H), 3.70 (s, 2H), 2.89 (s, 6H), 2.74-2.66 (m, 2H), 2.44 (d, J = 6.4Hz, 2H), 1.80 (d, J = 10.8Hz, 2H), 1.64-1.61 (m, 1H), 1.27-1.17 (m, 2H) ; HPLC (Method 9) 95.8% (area under the curve), t _R = 6.53 minutes; ESI + APCI-MS m / z 535 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl yl) amino) methyl) piperidine-1-carboxylate (tert -butyl 3 - ((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ) pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidine-1-carboxylate) 6-8o (Example 2-79)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a Same method using tert-butyl 3-formylpiperidine-1-carboxylate 7o Preparation of 3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 6-8o and obtained as an off-white solid (23% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H) 6.86 (s, 1H), 6.78 (dd, J = 2.4, 7.6Hz, 1H), 6.62 (s, 1H), 4.00 (s, 3H), 3.93 (s, 4H), 3.79 (t, J = 12.8Hz, 3H), 2.76-2.67 (m, 2H) , 2.44-2.32 (m, 4H), 1.87-1.72 (m, 3H), 1.58-1.54 (m, 4H), 1.38 (s, 9H), 1.30-1.21 (m, 4H), 1.18-1.10 (m, 1H); HPLC (method 10) 99.2% (area under the curve), t _R = 6.85 minutes; ESI + APCI-MS m / z 598 [M + H] ⁺ .

2-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Amino) amino) methyl) -N , N -dimethylaniline 6-8p (Example 2-15)

With 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2,5-Dimethoxybenzyl) methylamine 6-8a Using the same method, 2-((dimethylamino) benzaldehyde) 6-7p was used to prepare 2-(( ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino ) Methyl) -N , N -dimethylaniline 6-8p and obtained as an off-white solid (23% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 8.00 (s, 1H), 7.44 (d, J = 6.8Hz, 1H) , 7.29 (d, J = 7.6Hz, 1H), 7.18 (d, J = 7.6Hz, 1H), 7.10-7.06 (m, 1H), 6.86 (s, 1H), 6.79 (dd, J = 5.6,7.6 Hz, 1H), 6.66 (s, 1H), 4.00 (s, 5H), 3.93 (s, 3H), 3.81 (d, J = 12.8Hz, 2H), 2.77-2.71 (m, 4H), 2.66 (s , 6H), 1.85-1.76 (m, 3H), 1.37-1.23 (m, 2H); HPLC (method 10) 95.5% (area under the curve), t _R = 6.85 minutes; ESI + APCI-MS m / z 534 [M + H] ⁺ .

Preparation of ((1- (2-Aminopyridin-4-yl) pyrrolidin-3-yl) methyl) amino formate 7-3

To a solution of 4-chloropyridine-2-amine 7-1 (500 mg, 3.90 mmol) in a mixture of n -butanol: N , N -diisopropylethylamine (10 mL / 5 mL), (pyrrolidine- 3- ylmethyl) carbamic acid tert-butyl (tert -butyl (pyrrolidin-3- ylmethyl) carbamate) 7-2 (937mg, 4.68mmol). The reaction mixture was heated in a sealed tube at 120 ° C for 24 hours. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc and differentiate saturated aqueous NaHCO ₃ (100mL / 50mL). The layers were separated, and the EtOAc layer was washed with brine (50 mL), dried over anhydrous Na ₂ SO _4, filtered and concentrated. The residue was triturated with hexane, filtered and dried to obtain ((1- (2-aminopyridin-4-yl) pyrrolidin-3-yl) methyl) tert-butyl aminoformate 7-3 (900 mg, 79%), as an off-white solid, which was used directly in the next step without further purification. ESI + APCI-MS m / z 293 [M + H] ⁺ .

Tert-butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl ) Urethane hydrobromide ( tert -butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3-yl) Preparation of methyl) carbamate hydrobromide) 7-5

Tert-butyl ((1- (2-aminopyridin-4-yl) pyrrolidin-3-yl) methyl) carbamate 7-3 (800 mg, 2.73 in acetone (15 mL) at 75 ° C) mmol) and 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 7-4 (880 mg, 3.01 mmol) were heated for 16 hours. The reaction mixture was cooled to room temperature. The formed precipitate was collected by filtration, washed with hexane (200 mL) and dried to give tert-butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) carbamate hydrobromide 7-5 (600 mg, 45%) as an off-white solid.

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 12.99 (s, 1H), 8.49 (d, J = 7.6 Hz, 1H), 8.22 (s, 1H), 7.88 (s, 1H), 7.06 (t, J = 5.2Hz, 1H), 6.98 (s, 1H), 6.92 (d, J = 8.0Hz, 1H), 6.28 (s, 1H), 4.05 (s, 3H), 3.98 (s, 3H), 3.52- 3.44 (m, 3H), 3.18-3.16 (m, 1H), 3.03 (t, J = 6.8Hz, 2H), 2.51-2.49 (m, 1H), 2.12-2.08 (m, 1H), 1.87-1.72 ( m, 1H), 1.39 (s, 9H); ESI + APCI MS m / z 487 [M + H] ⁺ .

(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methylamine 7-6 Preparation

For tert-butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- in CH ₂ Cl ₂ (10 mL) ) (Pyrrolidin-3-yl) methyl) carbamate hydrobromide 7-5 (600 mg, 1.23 mmol) suspension, HCl solution (4.0 M in 1,4-dioxane, 5 mL) was added The reaction mixture was stirred at room temperature for 16 hours. By filtration, the resulting solid was collected and washed with CH ₂ Cl _2. Then, the solid was suspended in water (15 mL) and basified with a saturated sodium bicarbonate solution (15 mL) by stirring at room temperature for 1 hour. The solid was collected by filtration, washed with water and dried to give (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidin-3-yl) methylamine 7-6, which was used directly in the next step without further purification. ESI + APCI MS m / z 387 [M + H] ⁺ .

4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl (Amino) amino) methyl) -N , N , 3-trimethylaniline 7-8a (Example 2-52)

For (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine in CH ₃ OH (10 mL)- 3-yl) methylamine 7-6 (150 mg, 0.38 mmol) and 4- (dimethylamino) -2-methylbenzaldehyde (4- (dimethylamino) -2-methylbenzaldehyde) 7-7a (76 mg, 0.46 mmol) solution, acetic acid (0.1 mL) was added, and the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (60 mg, 0.97 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate solution (20 mL) and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined were washed with brine (20mL) The organic extracts were dried over anhydrous Na ₂ SO _4, filtered and concentrated. By combination-rapid colorimetric analysis [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)], 4-(((((1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N , N , 3-trimethyl Aniline 7-8a (25 mg, 12%) as an off-white solid.

¹ H NMR (400MHz, CDCl ₃ ): δ 8.38 (s, 1H), 7.83 (d, J = 7.2Hz, 1H), 7.80 (s, 1H), 7.13 (d, J = 8.0Hz, 1H), 6.58 -6.54 (m, 3H), 6.42 (s, 1H), 6.32 (dd, J = 2.4, 7.6Hz, 1H), 3.99 (s, 3H), 3.95 (s, 3H), 3.72 (s, 2H), 3.53-3.51 (m, 1H), 3.45-3.32 (m, 2H), 3.13-3.09 (m, 1H), 2.92 (s, 6H), 2.79-2.69 (m, 2H), 2.58-2.49 (m, 1H ), 2.35 (s, 3H), 2.22-2.15 (m, 1H), 1.83-1.74 (m, 1H); HPLC (Method 7) 91.7% (area under the curve), t _R = 6.45 minutes; ESI + APCI- MS m / z 534 [M + H] ⁺ .

4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl (Amino) amino) methyl) -N , N , 2-trimethylaniline 7-8b (Example 2-57)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a, using 4- (dimethylamino) -3-methylbenzaldehyde 7-7b to prepare 4 -((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl ) Amino) methyl) -N , N , 2-trimethylaniline 7-8b and obtained as an off-white solid (12% yield).

¹ H NMR (400MHz, CDCl ₃ ): δ 8.39 (s, 1H), 7.83 (d, J = 7.2Hz, 1H), 7.80 (s, 1H), 7.12 (d, J = 8.0Hz, 1H), 6.58 -6.54 (m, 3H), 6.40 (s, 1H), 6.31 (dd, J = 2.0, 7.2Hz, 1H), 3.99 (s, 3H), 3.94 (s, 3H), 3.72 (s, 2H), 3.52 (t, J = 9.2Hz, 1H), 3.45-3.31 (m, 2H), 3.13-3.09 (m, 1H), 2.92 (s, 6H), 2.79-2.69 (m, 2H), 2.58-2.50 ( m, 1H), 2.35 (s, 3H), 2.22-2.11 (m, 1H), 1.83-1.74 (m, 1H); HPLC (method 7) 93.5% (area under the curve), t _R = 6.45 minutes; ESI + APCI-MS m / z 534 [M + H] ⁺ .

4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl (Amino) amino) methyl) -3-methoxy- N , N -dimethylaniline 7-8c (Example 2-55)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a using 4- (dimethylamino) -2-methoxybenzaldehyde (4- ( dimethylamino) -2-methoxybenzaldehyde) 7-7c Preparation of 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) methyl) amino) methyl) -3-methoxy- N , N -dimethylaniline 7-8c and obtained as an off-white solid (yield 14%).

¹ H NMR (300MHz, CDCl ₃ ): δ 8.38 (s, 1H), 7.84-7.80 (m, 2H), 7.06 (d, J = 9.0Hz, 1H), 6.56 (s, 1H), 6.39 (s, 1H), 6.32-6.26 (m, 3H), 3.99 (s, 3H), 3.94 (s, 3H), 3.84 (s, 3H), 3.73 (s, 2H), 3.52 (t, J = 7.8Hz, 1H ), 3.44-3.29 (m, 2H), 3.10-3.04 (m, 1H), 2.95 (s, 6H), 2.72-2.61 (m, 2H), 2.56-2.46 (m, 1H), 2.20-2.15 (m 1H), 1.80-1.70 (m, 1H); HPLC (method 7) 97.3% (area under the curve), t _R = 6.65 minutes; ESI + APCI-MS m / z 550 [M + H] ⁺ .

2-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl (Amino) amino) methyl) -N , N -dimethylaniline 7-8d (Example 2-13)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a, 2-((((( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl ) -N , N -dimethylaniline 7-8d and obtained as an off-white solid (12% yield).

¹ H NMR (300 MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2 Hz, 1 H), 8.15 (s, 1 H), 7.93 (s, 1 H), 7.43 (d, J = 7.5 Hz, 1 H) , 7.18 (t, J = 7.2Hz, 1H), 7.09-6.98 (m, 2H), 6.85 (s, 1H), 6.46 (d, J = 7.5Hz, 1H), 6.18 (s, 1H), 3.99 ( s, 3H), 3.92 (s, 3H), 3.79 (s, 2H), 3.46 (t, J = 9.0Hz, 1H), 3.40-3.36 (m, 1H), 3.30-3.25 (m, 1H), 3.08 (t, J = 6.3Hz, 1H), 2.64-2.58 (m, 9H), 2.16-2.08 (m, 1H), 1.77-1.68 (m, 1H); HPLC (method 14) 98.2% (area under the curve) , T _R = 6.72 minutes; ESI + APCI-MS m / z 520 [M + H] ⁺ .

5-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formaldehyde (Amino) amino) methyl) -2-methoxyphenol 7-8e (Example 2-42)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a The same method was used to prepare 5-(((((( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl ) -2-methoxyphenol 7-8e and obtained as an off-white solid (yield 14%).

¹ H NMR (400MHz, CD ₃ OD): δ 8.98 (d, J = 7.2Hz, 1H), 7.92 (s, 1H), 7.78 (s, 1H), 6.79-6.75 (m, 2H), 6.71-6.67 (m, 2H), 6.38 (dd, J = 2.0, 7.2 Hz, 1H), 6.14 (s, 1H), 3.91 (s, 3H), 3.84 (s, 3H), 3.73 (s, 3H), 3.61 ( s, 2H), 3.46-3.42 (m, 1H), 3.38-3.31 (m, 1H), 3.28-3.22 (m, 1H), 2.95 (t, J = 8.0Hz, 1H), 2.62-2.58 (m, 2H), 2.47-2.40 (m, 1H), 2.14-2.09 (m, 1H), 1.69-1.60 (m, 1H); HPLC (method 7) 91.1% (area under the curve), t _R = 6.53 minutes; ESI + APCI-MS m / z 523 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- ( Preparation of 2,4-dimethoxybenzyl) methylamine 7-8f (Example 2-34)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a, prepared using 2,4-dimethoxybenzaldehyde 7-7f 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( 2,4-dimethoxybenzyl) methylamine 7-8f and obtained as an off-white solid (yield 10%).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.5Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 7.23 (d, J = 8.1Hz, 1H) , 6.85 (s, 1H), 6.54 (s, 1H), 6.50-6.45 (m, 2H), 6.18 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.78 (s, 3H ), 3.74 (s, 3H), 3.70 (s, 2H), 3.49-3.43 (m, 1H), 3.34-3.28 (m, 2H), 3.09-3.04 (m, 1H), 2.64-2.52 (m, 3H ), 2.20-2.10 (m, 1H), 1.78-1.69 (m, 1H); HPLC (Method 7) 95.8% (area under the curve), t _R = 6.71 minutes; ESI + APCI-MS m / z 537 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( 4-methoxy-3-methylbenzyl) methylamine (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin -3-yl) - N - ( 4-methoxy-3-methylbenzyl) methanamine) 7-8g prepared (Examples 2-22)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a The same method was used to prepare 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (4- methoxy 7-8 g of 3-methylbenzyl) methylamine was obtained as an off-white solid (yield 15%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.93 (s, 1H), 7.13-7.11 (m, 2H), 6.86- 6.85 (m, 2H), 6.46 (dd, J = 2.0, 7.6Hz, 1H), 6.18 (s, 1H), 3.99 (s, 3H), 3.92 (s, 3H), 3.75 (s, 3H), 3.64 (br s, 2H), 3.45 (t, J = 9.6Hz, 1H), 3.29-3.25 (m, 1H), 3.08-3.04 (m, 1H), 2.60-2.50 (m, 4H), 2.12-2.08 ( m, 4H), 1.81-1.68 (m, 1H); HPLC (method 7) 97.9% (area under the curve), t _R = 6.96 minutes; ESI + APCI-MS m / z 521 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 2,4-difluorobenzyl) methylamine 7-8h (Example 2-26)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a The same method was used to prepare 1--7-h using 2,4-difluorobenzaldehyde 7-7h (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (2, 4-Difluorobenzyl) methylamine 7-8h and obtained as an off-white solid (13% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.14 (s, 1H), 7.94 (s, 1H), 7.56-7.50 (m, 1H), 7.21- 7.16 (m, 1H), 7.09-7.05 (m, 1H), 6.85 (s, 1H), 6.47 (dd, J = 2.4,7.6Hz, 1H), 6.18 (s, 1H), 4.00 (s, 3H) , 3.93 (s, 3H), 3.75 (s, 2H), 3.48-3.44 (m, 1H), 3.32-3.26 (m, 1H), 3.09-3.04 (m, 1H), 2.60-2.54 (m, 4H) , 2.15-2.07 (m, 1H), 1.77-1.86 (m, 1H); HPLC (method 15) 98.8% (area under the curve), t _R = 6.65 minutes; ESI + APCI-MS m / z 513 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( 4-fluoro-3-methylbenzyl) methylamine (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) pyrrolidin-3 -yl) - N - (4- fluoro-3-methylbenzyl) methanamine) prepared 7-8i (Example 2-21);

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a, 4-fluoro-3-methylbenzaldehyde 7-7i was used to prepare 1- (1- (2 - (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - (4- fluoro-3- Benzyl) methylamine 7-8i and obtained as an off-white solid (yield 10%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.45 (d, J = 7.6Hz, 1H), 8.14 (s, 1H), 8.07 (s, 1H), 7.60 (t, J = 7.2Hz, 1H) , 7.16-7.10 (m, 2H), 6.93 (s, 1H), 6.75 (br s, 1H), 6.31 (s, 1H), 4.13 (s, 2H), 4.03 (s, 3H), 3.96 (s, 3H), 3.66-3.62 (m, 1H), 3.56-3.52 (m, 1H), 3.45-3.37 (m, 2H), 3.11 (br s, 2H), 2.84-2.78 (m, 1H), 2.42 (s , 3H), 2.27-2.21 (m, 1H), 1.93-1.84 (m, 1H); HPLC (method 7) 96.4% (area under the curve), t _R = 6.92 minutes; ESI + APCI-MS m / z 509 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 3-fluoro-4-methylbenzyl) methylamine 7-8j (Example 2-25)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a Same method using 3-fluoro-4-methylbenzaldehyde 7- 7j Preparation of 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(3-fluoro-4-methylbenzyl) methylamine 7-8j and obtained as an off-white solid (16% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.14 (s, 1H), 7.96 (s, 1H), 7.35-7.06 (m, 3H), 6.86 ( s, 1H), 6.49 (dd, J = 2.0, 7.2 Hz, 1H), 6.19 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.83 (br s, 2H), 3.50- 3.42 (m, 1H), 3.40-3.36 (m, 1H), 3.11-3.07 (m, 1H), 2.60-2.52 (m, 4H), 2.21 (s, 3H), 2.17-2.11 (m, 1H), 1.80-1.73 (m, 1H); HPLC (method 15) 99.0% (area under the curve), t _R = 6.75 minutes; ESI + APCI-MS m / z 509 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) - N - ( Preparation of 2-fluoro-4-methylbenzyl) methylamine 7-8k (Example 2-23)

With 4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Methyl) amino) methyl) -N , N , 3-trimethylaniline 7-8a Same method using 2-fluoro-4-methylbenzaldehyde 7- 7k Preparation of 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N -(2-fluoro-4-methylbenzyl) methylamine 7-8k and obtained as an off-white solid (yield 14%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 7.36 (t, J = 8.4Hz, 1H) , 7.006.97 (m, 2H), 6.86 (s, 1H), 6.47 (dd, J = 2.0, 7.2Hz, 1H), 6.18 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H ), 3.75 (s, 2H), 3.48-3.44 (m, 1H), 3.32-3.26 (m, 1H), 3.08-3.04 (m, 1H), 2.60-2.50 (m, 4H), 2.29 (s, 3H ), 2.13-2.07 (m, 1H), 1.77-1.68 (m, 1H); HPLC (method 7) 95.1% (area under the curve), t _R = 6.92 minutes; ESI + APCI-MS m / z 509 [M + H] ⁺ .

((1- (2-amino-4-yl) azetidin-3-yl) methyl) carbamic acid tert-butyl ester (tert -butyl ((1- (2 -aminopyridin-4-yl ) azetidin-3-yl) methyl) carbamate) 8-3

To a solution of 4-chloropyridine-2-amine 8-1 (2.50 g, 19.5 mmol) in isopropanol / N , N -diisopropylethylamine (50 mL / 25 mL) was added tert-butyl (aza Cyclobutane-3-ylmethyl) carbamate hydrochloride ( tert- butyl (azetidin-3-ylmethyl) carbamate hydrochloride) 8-2 (5.60 g, 25.4 mmol). The reaction mixture was heated in a sealed tube at 120 ° C for 24 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was distinguished between EtOAc and saturated sodium bicarbonate solution. The layers were separated; the organic layer was dried over sodium sulfate, filtered and concentrated. The residue was washed with hexane to give ((1- (2-aminopyridin-4-yl) azetidin-3-yl) methyl) aminocarboxylic acid tert-butyl ester 8-3 (5.2 g, 96 %) As an off-white solid, which was used directly in the next step without further purification. ESI + APCI-MS m / z 279 [M + H] ⁺ .

((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl ) carbamic acid tert-butyl ester (tert -butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) azetidin-3-yl) methyl Preparation of carbamate) 8-5

Tert-Butyl ((1- (2-aminopyridin-4-yl) azetidin-3-yl) methyl) carbamate 8-3 ( 10.0 g, 36.0 mmol) and 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 8-4 (13.5 g, 46.6 mmol) were heated for 16 hours. The reaction mixture was cooled to room temperature, and the white precipitate formed was collected by filtration and washed with hexane. The crude material was dissolved in water (200 mL) and a saturated sodium bicarbonate solution (200 mL), and stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and dried to give ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Azetane-3-yl) methyl) tert-butyl carbamate 8-5 (6.0 g, 36%) as an off-white solid. ESI + APCI-MS m / z 473 [M + H] ⁺ .

(1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methylamine 8 Preparation of -6

((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) aza in H ₂ O (40 mL) A suspension of cyclobutane-3-yl) methyl) carbamic acid tert-butyl ester 8-5 (6.00 g, 12.7 mmol) was added to concentrated HCL (con.HCl) (10 mL). The reaction mixture was heated at 100 ° C for 20 minutes. The reaction mixture was cooled to room temperature and basified with a saturated sodium bicarbonate solution (100 mL). The aqueous layer was extracted with CH ₂ Cl ₂ (2 × 100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to give (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) azetidin-3-yl) methylamine 8-6 (3.6 g, 77%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 6.85 (s, 1H),), 6.25 ( dd, J = 2.0, 7.2Hz, 1H), 6.11 (s, 1H), 3.99 (s, 3H), 3.93 (s, 3H), 3.89 (d, J = 3.6Hz, 2H), 3.61-3.57 (m , 2H), 2.77 (d, J = 6.8 Hz, 2H), 2.78-2.69 (m, 1H).

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine- Preparation of 3-yl) methylamine 8-8a (Examples 2-4)

(1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine in CH ₃ OH (5 mL) A suspension of alk-3-yl) methylamine 8-6 (60 mg, 0.16 mmol) and benzaldehyde (20 mg, 0.19 mmol), acetic acid (0.1 mL) was added, and the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (20 mg, 32 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with an aqueous sodium bicarbonate solution (10 mL), and the aqueous layer was extracted with CH ₂ Cl ₂ (2 × 10 mL). The combined were washed with brine (10 mL) The organic extracts were dried over anhydrous Na ₂ SO _4, filtered and concentrated. Combining-rapid colorimetric analysis [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to give N-benzyl-1- (1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methylamine 8-8a (20mg, 27%), off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 7.37-7.34 (m, 4H), 7.23 ( t, J = 7.2Hz, 1H), 6.85 (s, 1H), 6.25 (dd, J = 2.0,7.2Hz, 1H), 6.12 (s, 1H), 3.99 (s, 3H), 3.96-3.94 (m , 2H), 3.93 (s, 3H), 3.76 (bs, 2H), 3.60-3.57 (m, 2H), 2.89-2.79 (m, 3H); HPLC (Method 4) 97.2% (area under the curve), t _R = 6.60 minutes; ESI + APCI-MS m / z 463 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl)- Preparation of N- (4-fluorobenzyl) methylamine 8-8b (Example 2-6)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a Using the same method, 4-fluorobenzaldehyde 8-7b was used to prepare 1- (1- (2- (5-chloro-2,4-dimethoxy) phenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) - N - (4- fluorobenzyl) methylamine 8-8b, and to obtain an off-white solid (Yield 25%).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 7.39-7.36 (m, 2H), 7.15- 7.10 (m, 2H), 6.85 (s, 1H), 6.24 (dd, J = 2.0, 7.2Hz, 1H), 6.12 (s, 1H), 3.99 (s, 3H), 3.95-3.91 (m, 5H) , 3.70 (bs, 2H), 3.59-3.56 (m, 2H), 2.83-2.72 (m, 3H); HPLC (method 4) 99.2% (area under the curve), t _R = 6.63 minutes; ESI + APCI-MS m / z 481 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl)- Preparation of N- (2-fluorobenzyl) methylamine 8-8c (Example 2-68)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a Using the same method, 2-fluorobenzaldehyde 8-7c to prepare 1- (1- (2- (5-chloro-2,4-dimethoxy) phenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) - N - (2- fluorobenzyl) methylamine 8-8c, and to obtain an off-white solid (33% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 7.50-7.46 (m, 1H), 7.35- 7.26 (m, 1H), 7.19-7.12 (m, 2H), 6.85 (s, 1H), 6.25 (dd, J = 2.4, 7.6Hz, 1H), 6.15 (s, 1H), 3.99 (s, 3H) , 3.95-3.94 (m, 2H), 3.93 (s, 3H), 3.76 (bs, 2H), 3.59-3.54 (m, 2H), 2.83-2.76 (m, 3H); HPLC (Method 4) 98.5% ( Area under the curve), t _R = 6.62 minutes; ESI + APCI-MS m / z 481 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl)- Preparation of N- (3-fluorobenzyl) methylamine 8-8d (Example 2-74)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a Using the same method, 3-fluorobenzaldehyde 8-7d was used to prepare 1- (1- (2- (5-chloro-2,4-dimethoxy) phenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) - N - (3- fluorobenzyl) methylamine 8-8d, and to obtain an off-white solid (28% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 7.38-7.34 (m, 1H), 7.20- 7.17 (m, 2H), 7.06-7.02 (m, 1H), 6.85 (s, 1H), 6.25 (dd, J = 2.4, 7.6Hz, 1H), 6.12 (d, J = 1.6Hz, 1H), 3.99 (s, 3H), 3.96-3.94 (m, 2H), 3.93 (s, 3H), 3.74 (bs, 2H), 3.60-3.56 (m, 2H), 2.83-2.77 (m, 1H), 2.75-2.73 (m, 2H); HPLC (method 4) 99.30% (area under the curve), t _R = 6.62 minutes; ESI + APCI-MS m / z 481 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl)- Preparation of N- (2-methylbenzyl) methylamine 8-8e (Example 2-38)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a Using the same method, 2-methylbenzaldehyde 8-7e to prepare 1- (1- (2- (5-chloro-2,4-dimethyl) methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) - N - (2- methylbenzyl) methylamine 8-8e, and off-white A solid was obtained (36% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 7.32-7.30 (m, 1H), 7.18- 7.13 (m, 3H), 6.85 (s, 1H), 6.26 (dd, J = 2.4, 7.2Hz, 1H), 6.12 (s, 1H), 3.99 (s, 3H), 3.97-3.95 (m, 2H) , 3.93 (s, 3H), 3.69 (bs, 2H), 3.61-3.59 (m, 2H), 2.94-2.76 (m, 3H), 2.30 (s, 3H); HPLC (method 7) 99.4% (under the curve Area), t _R = 6.75 minutes; ESI + APCI-MS m / z 477 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl)- Preparation of N- (4-methylbenzyl) methylamine 8-8f (Example 2-43)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a Using the same method, 4-methylbenzaldehyde 8-7f to prepare 1- (1- (2- (5-chloro-2,4-dimethyl) methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) - N - (4- methylbenzyl) methylamine 8-8f, and off-white A solid was obtained (28% yield).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.98 (s, 1H), 7.25 (d, J = 6.6Hz, 2H) , 7.16 (d, J = 6.6Hz, 2H), 6.85 (s, 1H), 6.26 (dd, J = 2.4, 7.2Hz, 1H), 6.15 (s, 1H), 4.00 (s, 3H), 3.96- 3.90 (m, 5H), 3.75 (bs, 2H), 3.62-3.55 (m, 2H), 2.85-2.72 (m, 3H), 2.28 (s, 3H); HPLC (method 7) 99.3% (area under the curve ), T _R = 7.25 minutes; ESI + APCI-MS m / z 477 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl)- Preparation of 8-8 g of N- (3-methylbenzyl) methylamine (Example 2-56)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a, 1- (1- (2- (5-chloro-2,4-dimethyl) was prepared using 8-7 g of 3-methylbenzaldehyde methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) - N - (3- methylbenzyl) methylamine 8-8g, and off-white A solid was obtained (34% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.98 (s, 1H), 7.23-7.14 (m, 3H), 7.05 ( d, J = 6.8Hz, 1H), 6.85 (s, 1H), 6.26 (dd, J = 2.4, 7.2Hz, 1H), 6.15 (s, 1H), 3.99 (s, 3H), 3.96-3.95 (m , 2H), 3.93 (s, 3H), 3.73 (bs, 2H), 3.60-3.57 (m, 2H), 2.91-2.81 (m, 3H), 2.29 (s, 3H); HPLC (Method 4) 98.9% (Area under the curve), t _R = 6.69 minutes; ESI + APCI-MS m / z 477 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3- (Methyl) methyl) amino) methyl) -N , N -dimethylaniline 8-8h (Example 2-18)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a The same method was used to prepare 4-((((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -N , N -dimethylaniline 8-8h and obtained as an off-white solid (19% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 7.16 (d, J = 8.8Hz, 2H) , 6.85 (s, 1H), 6.68 (d, J = 8.4Hz, 2H) 6.25 (dd, J = 2.0, 7.2Hz, 1H), 6.12 (s, 1H), 3.99 (s, 3H), 3.96-3.94 (m, 2H), 3.93 (s, 3H), 3.66 (bs, 2H), 3.59-3.56 (m, 2H), 2.86 (s, 6H), 2.82-2.79 (m, 3H); HPLC (Method 4) 97.2% (area under the curve), t _R = 6.42 minutes; ESI + APCI-MS m / z 506 [M + H] ⁺ .

2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3- (Methyl) methyl) amino) methyl) -N , N -dimethylaniline 8-8i (Example 2-77)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a, 2-((((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -N , N -dimethylaniline 8-8i and obtained as an off-white solid (31% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.35 (d, J = 7.2Hz, 1H), 8.12 (s, 1H), 8.04 (s, 1H), 7.52-7.50 (m, 1H), 7.39 ( t, J = 7.2Hz, 1H), 7.28 (d, J = 7.6Hz, 1H), 7.17 (t, J = 7.6Hz, 1H), 6.88 (s, 1H), 6.38-6.33 (m, 1H), 6.20 (d, J = 2.0Hz, 1H), 4.23 (bs, 2H), 4.06 (t, J = 8.0Hz, 2H), 4.01 (s, 3H), 3.93 (s, 3H), 3.75-3.71 (m , 2H), 3.27 (d, J = 6.4 Hz, 2H), 3.13-3.06 (m, 1H), 2.66 (s, 6H); HPLC (method 4) 99.0% (area under the curve), t _R = 6.62 minutes ; ESI + APCI-MS m / z 506 [M + H] ⁺ .

N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) Preparation of (methyl) -3,3-dimethylbut-1-amine 8-8j (Example 2-40)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a Using the same method, 3,3-dimethylbutanal (3,3-dimethylbutanal) 8-7j was used to prepare N -((1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) -3,3-dimethylbut-1 -Amine 8-8j and obtained as an off-white solid (29% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 6.85 (s, 1H), 6.25 (dd, J = 2.0, 7.6Hz, 1H), 6.13 (s, 1H), 3.99 (s, 3H), 3.98-3.95 (m, 2H), 3.93 (s, 3H), 3.57-3.56 (m, 2H), 2.81 -2.71 (m, 3H), 1.38-1.31 (m, 2H), 0.9 (s, 9H); HPLC (Method 4) 96.4% (area under the curve), t _R = 6.69 minutes; ESI + APCI-MS m / z 457 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl)- N- (cyclopentylmethyl) methylamine (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) azetidin-3-yl ) - N - (cyclopentylmethyl) methanamine ) 8-8k prepared (Example 2-9)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine 7-yl) azetidin-3-yl) - N - (cyclopentylmethyl) methanamine 8-8k, and to obtain an off-white solid (yield 29%).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.2 Hz, 1H), 8.15 (s, 1H), 7.98 (s, 1H), 6.86 (s, 1H), 6.27 (dd, J = 2.0, 7.2Hz, 1H), 6.15 (s, 1H), 3.99 (s, 3H), 3.97-3.96 (m, 2H), 3.93 (s, 3H), 3.64-3.61 (m, 2H), 2.95 -2.91 (m, 3H), 2.67-2.62 (m, 2H), 2.07-2.01 (m, 1H), 1.76-1.70 (m, 2H), 1.69-1.53 (m, 4H), 1.29-1.15 (m, 2H); HPLC (method 4) 95.7% (AUC), t _R = 6.59 minutes; ESI + APCI-MS m / z 455 [m + H] +.

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl)- Preparation of N- (cyclohexylmethyl) methylamine 8-8l (Examples 2-16)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a, 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine 7-yl) azetidin-3-yl) - N - (cyclohexylmethyl) methanamine 8-8l, and to obtain an off-white solid (22% yield).

¹ H NMR (300MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.98 (s, 1H), 6.85 (s, 1H), 6.26 (d, J = 6.6Hz, 1H), 6.14 (s, 1H), 3.99 (s, 3H), 3.97-3.94 (m, 2H), 3.93 (s, 3H), 3.70-3.59 (m, 2H), 2.91-2.89 (m, 3H), 2.49-2.48 (m, 2H), 1.75-1.55 (m, 4H), 1.55-1.33 (m, 1H), 1.23-1.17 (m, 4H), 1.07-0.97 (m, 2H) ; HPLC (Method 4) 98.1% (area under the curve), t _R = 6.71 minutes; ESI + APCI-MS m / z 469 [M + H] ⁺ .

2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3- yl) methyl) amino) methyl) piperidine-1-carboxylate (tert -butyl 2 - ((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 Preparation of 2,2- a ] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate) 8-8m (Example 2-61)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a was prepared in the same manner as 2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 8-8m, and obtained as an off-white solid (yield 37 %).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 6.85 (s, 1H), 6.26 (dd, J = 2.4, 7.2Hz, 1H), 6.15 (d, J = 2.0Hz, 1H), 4.14 (bs, 1H), 3.99 (s, 3H), 3.97-3.93 (m, 5H), 3.79-3.74 (m , 1H), 3.59-3.56 (m, 2H), 2.82-2.76 (m, 4H), 2.67-2.66 (m, 3H), 1.73-1.70 (m, 1H), 1.59-1.48 (m, 4H), 1.38 (s, 9H); HPLC (method 4) 98.3% (area under the curve), t _R = 6.79 minutes; ESI + APCI-MS m / z 570 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3- yl) methyl) amino) methyl) piperidine-1-carboxylate (tert -butyl 3 - ((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 (2- a ) pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate) 8-8n (Example 2-62)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a was prepared in the same way as 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 8-8n and obtained as an off-white solid (yield 47 %).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 6.85 (s, 1H), 6.24 (d, J = 4.0Hz, 1H), 6.15 (s, 1H), 3.99 (s, 3H), 3.97-3.95 (m, 3H), 3.93 (s, 3H), 3.77-3.74 (m, 1H), 3.62-3.56 (m, 2H), 2.78-2.67 (m, 4H), 2.41-2.35 (m, 2H), 1.75-1.73 (m, 1H), 1.59-1.50 (m, 2H), 1.38 (s, 9H), 1.37 -1.26 (m, 2H), 1.10-1.07 (m, 1H); HPLC (method 7) 99.3% (area under the curve), t _R = 7.25 minutes; ESI + APCI-MS m / z 570 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3- yl) methyl) amino) methyl) piperidine-1-carboxylate (tert -butyl 4 - ((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 Preparation of 2,2- a ] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate) 8-8o (Example 2-8)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a, 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 8-8o and obtained as an off-white solid (yield 33 %).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 6.85 (s, 1H), 6.26 (dd, J = 2.4, 7.2 Hz, 1H), 6.12 (d, J = 2.0 Hz, 1H), 3.99 (s, 3H), 3.93-3.91 (m, 7H), 3.58-3.55 (m, 2H), 2.83-2.75 (m, 4H), 2.41 (d, J = 6.4 Hz, 2H), 1.67 (d, J = 8.8 Hz, 2H), 1.61-1.51 (m, 1H), 1.38 (s, 10H), 1.0-0.91 ( m, 2H); HPLC (method 7) 98.7% (area under the curve), t _R = 6.83 minutes; ESI + APCI-MS m / z 570 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3- Of methyl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 8-8p (Example 2-7)

N -benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine Alkyl-3-yl) methylamine 8-8a was prepared in the same way as 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) azetidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 8-8p, obtained as an off-white solid (yield 45 %).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.28 (d, J = 7.2Hz, 1H), 8.15 (s, 1H), 7.97 (s, 1H), 6.85 (s, 1H), 6.26 (dd, J = 2.4, 7.2Hz, 1H), 6.12 (d, J = 2.0Hz, 1H), 3.99 (s, 3H), 3.96-3.94 (m, 2H), 3.93 (s, 3H), 3.58-3.56 (m , 2H), 3.32-3.26 (1H), 3.21-3.18 (m, 2H), 3.16-3.14 (m, 1H), 2.93-2.88 (m, 1H), 2.77-2.67 (m, 3H), 2.30-2.25 (m, 1H), 1.99-1.90 (m, 1H), 1.60-1.58 (m, 2H), 1.39 (s, 10H); HPLC (method 7) 98.2% (area under the curve), t _R = 6.86 minutes; ESI + APCI-MS m / z 556 [M + H] ⁺ .

Scheme 14

(2- (1- (2-Aminopyridin-4-yl) piperidin-4-yl) ethyl) tert-butyl ( amino) carboxylic acid tert-butyl (2- (1- (2-aminopyridin-4- Preparation of yl) piperidin-4-yl) ethyl) carbamate) 9-3

To a solution of 4-chloropyridine-2-amine 9-1 (2.0 g, 16 mmol) in a mixture of isopropanol and N , N' -diisopropylethylamine (40 mL / 20 mL) was added (2- (piperidine 4-yl) ethyl) t-butylaminoformate 9-2 (5.3 g, 23 mmol). The reaction mixture was heated in a sealed tube at 120 ° C for 24 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between EtOAc and differentiate saturated aqueous NaHCO ₃ (300mL / 100mL). The layers were separated, the EtOAc layer was washed with brine (100 mL), dried over Na ₂ SO _4, filtered and concentrated. The residue was triturated with hexane and dried to give (2- (1- (2-aminopyridin-4-yl) piperidin-4-yl) ethyl) aminocarboxylic acid tert-butyl 9-3 (3.1 g , 62%), as an off-white solid, which was used directly in the next step without further purification. ESI + APCI-MS m / z 321 [M + H] ⁺ .

(2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) Tert-butyl ( 2- (1- (2- (5- (chloro (2,4-dimethoxyphenyl) imidazo [1,2- a ) pyridin-7-yl) piperidin-4-yl) Preparation of ethyl) carbamate) 9-5

Tert-butyl 2- (1- (2-aminopyridin-4-yl) piperidin-4-yl) ethyl) aminoformate 9-3 (1.0 g in acetone (20 mL) at 75 ° C) , 3.1 mmol) and 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 9-4 (1.0 g, 3.4 mmol) were heated for 16 hours. The reaction mixture was cooled to room temperature. The formed precipitate was collected by filtration, washed with hexane (100 mL) and dried. The hydrobromide was dissolved in a saturated sodium bicarbonate solution (1200 mL) and stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and dried to give (2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) piperidine-4-yl) ethyl) t-butylaminocarbamate 9-5 (650 mg, 41%) as an off-white solid. ESI + APCI-MS m / z 515 [M + H] ⁺ .

2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl-1- Amine (2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethan-1-amine) 9-6 Preparation

(2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl in CH ₂ Cl ₂ (10 mL) ) Piperidin-4-yl) ethyl) urethane tert-butyl 9-5 (500 mg, 0.9 mmol) suspension, added HCl solution (4.0 M in 1,4-dioxane, 2 mL), and The reaction mixture was stirred at room temperature for 16 hours. The solid obtained in the reaction was collected by filtration, washed with CH ₂ Cl ₂ (20 mL) and dried. Then, the solid was suspended in water (10 mL) and basified with a saturated sodium bicarbonate solution (10 mL) by stirring at room temperature for 1 hour. The solid was collected by filtration, washed with water and dried to give 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Yl) piperidin-4-yl) ethyl-1-amine 9-6 (180 mg, 45%) as an off-white solid. ESI + APCI-MS m / z 415 [M + H] ⁺ .

3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester ( tert -butyl 3-((((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ Preparation of 1,2- a ] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) pyrrolidine-1-carboxylate) 9-8a (Example 2-102)

2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) piperidine in CH ₃ OH (5 mL) 4-yl) ethan-1-amine 9-6 (100mg, 0.24mmol) and 3-acyl pyrrolidine-1-carboxylate (tert -butyl 3-formylpyrrolidine-1 -carboxylate) 9- 7a (72 mg, 0.36 mmol) suspension, acetic acid (0.1 mL) was added, and the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (45 mg, 0.72 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate (20 mL), and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined were washed with brine (20mL) The organic extracts were dried over anhydrous Na ₂ SO _4, filtered and concentrated. The residue was purified by combinatorial-rapid chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to obtain 3-(((2- (1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) pyrrolidine Tert-butyl-1-carboxylic acid 9-8a (20 mg, 14%) as an off-white solid.

¹ H NMR (400MHz, CD ₃ OD): δ 8.02 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.86 (s, 1H), 6.69 (s, 1H), 6.66 (dd, J = 2.4,7.6Hz, 1H), 6.56 (d, J = 2.4Hz, 1H), 3.92 (s, 3H), 3.84 (s, 3H), 3.73 (d, J = 12.8Hz, 2H), 3.50-3.42 (m, 1H), 3.38-3.32 (m, 1H), 2.92-2.84 (m, 1H), 2.73-2.53 (m, 6H), 2.32-2.26 (m, 1H), 1.96 (br s, 1H), 1.75 (d, J = 13.2 Hz, 2H), 1.57-1.41 (m, 4H), 1.36 (s, 9H), 1.31-1.18 (m, 3H); HPLC (method 7) 99.1% (area under the curve), t _R = 6.82 minutes; ESI + APCI-MS m / z 598 [M + H] ⁺ .

2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of cyclohexylmethyl) ethyl-1-amine 9-8b (Example 2-107)

With 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 9-8a The same method was used to prepare 2- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - (cyclohexylmethyl) ethan-l Amine 9-8b and obtained as an off-white solid (10% yield).

¹ H NMR (400MHz, CD ₃ OD): δ 8.02 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 6.69 (s, 1H), 6.65 (dd, J = 2.4,7.6Hz, 1H), 6.55 (d, J = 2.0Hz, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 3.72 (d, J = 12.4Hz, 2H), 2.72-2.64 (m, 4H), 2.46 (d, J = 6.8 Hz, 2H), 1.75-1.58 (m, 7H), 1.49-1.43 (m, 3H), 1.30-1.08 (m, 6H), 0.91-0.81 (m , 2H); HPLC (Method 4) 98.3% (area under the curve), t _R = 6.84 minutes; ESI + APCI-MS m / z 511 [M + H] ⁺ .

4-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Ethyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester ( tert -butyl 4-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2- a ] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) piperidine-1-carboxylate) 9-8c (Example 2-96)

With 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 9-8a In the same manner, 4-methylpyridin-1-carboxylic acid tert-butyl ester (tert-butyl 4 -formylpiperidine-1-carboxylate) 9-7c Preparation of 4-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine -7-yl) piperidin-4-yl) ethyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 9-8c was obtained as an off-white solid (12% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.77 (d, J = 6.0Hz, 1H), 6.62 (s, 1H), 4.00 (s, 3H), 3.93 (br s, 5H), 3.76 (d, J = 12.0Hz, 2H), 2.72-2.66 (m, 4H) , 2.50-2.40 (m, 2H), 2.37 (d, J = 6.8Hz, 2H), 1.75-1.65 (m, 4H), 1.53 (br s, 2H), 1.38 (s, 11H), 1.26-1.18 ( m, 2H), 0.99-0.91 (m, 2H); HPLC (method 7) 98.1% (area under the curve), t _R = 7.76 minutes; ESI + APCI-MS m / z 612 [M + H] ⁺ .

3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Ethyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester ( tert -butyl 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ Preparation of 1,2- a ] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) piperidine-1-carboxylate9-8d (Example 2-110)

With 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 9-8a The same method is used to prepare 3-methylpyridin-1-carboxylic acid tert-butyl ester 9-7d. 3 -(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) Ethyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 9-8d and obtained as an off-white solid (yield 10%).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.0, 7.6 Hz, 1H), 6.62 (d, J = 2.0 Hz, 1H), 4.00 (s, 3H), 3.93 (s, 4H), 3.78-3.72 (m, 3H), 2.79-2.67 (m , 3H), 2.59-2.55 (m, 2H), 2.45-2.39 (m, 3H), 1.74 (d, J = 10.8Hz, 3H), 1.59-1.49 (m, 3H), 1.38 (s, 11H), 1.30-1.08 (m, 4H); HPLC (method 16) 97.2% (area under the curve), t _R = 6.95 minutes; ESI + APCI-MS m / z 612 [M + H] ⁺ .

N -benzyl-2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Preparation of ethyl-1-amine 9-8e (Example 2-111)

With 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 9-8a, N -benzyl-2- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl-1-amine 9-8e as an off-white solid Obtained (16% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.34-7.28 (m, 4H), 7.24- 7.20 (m, 1H), 6.86 (s, 1H), 6.77 (dd, J = 2.4,7.6Hz, 1H), 6.61 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s , 3H), 3.75 (d, J = 12.4Hz, 2H), 3.70 (s, 2H), 2.72-2.66 (m, 2H), 2.56-2.51 (m, 2H), 1.71 (d, J = 12.0Hz, 2H), 1.60-1.50 (m, 1H), 1.43-1.37 (m, 2H), 1.25-1.17 (m, 2H); HPLC (Method 16) 99.3% (area under the curve), t _R = 6.77 minutes; ESI + APCI-MS m / z 505 [M + H] ⁺ .

4-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Ethyl) amino) methyl) benzonitrile (4-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl ) piperidin-4- yl) ethyl) amino) methyl) benzonitrile) 9-8f (Example 2-95)

With 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 9-8a, 4-(((2- (1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) benzonitrile 9-8f as an off-white solid Obtained (14% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.2Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 7.78 (d, J = 8.0Hz, 2H) , 7.54 (d, J = 8.0Hz, 2H), 6.86 (s, 1H), 6.77 (dd, J = 2.0, 7.6Hz, 1H), 6.62 (s, 1H), 4.00 (s, 3H), 3.93 ( s, 3H), 3.77-3.74 (m, 4H), 2.72-2.66 (m, 2H), 2.51-2.49 (m, 2H), 1.71 (d, J = 12.0Hz, 2H), 1.55 (brs, 1H) , 1.42-1.38 (m, 2H), 1.24-1.16 (m, 2H); HPLC (Method 4) 98.8% (area under the curve), t _R = 6.73 minutes; ESI + APCI-MS m / z 530 [M + H] ⁺ .

((1- (2-Aminopyridin-4-yl) piperidin-3-yl) methyl) tert-butyl carbamate (tert -butyl ((1- (2-aminopyridin-4-yl) piperidin- Preparation of 3-yl) methyl) carbamate) 10-3

To a solution of 4-chloropyridine-2-amine 10-1 (2.00 g, 15.6 mmol) in a mixture of isopropanol and N , N' -diisopropylethylamine (40 mL / 20 mL), (piperidine- 3- ylmethyl) carbamic acid tert-butyl (tert -butyl (piperidin-3- ylmethyl) carbamate) 10-2 (4.34g, 20.3mmol). The reaction mixture was heated in a sealed tube at 120 ° C for 24 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo . The residue was partitioned between EtOAc and saturated aqueous NaHCO _3: distinguishing between (300mL 100mL). The layers were separated, the EtOAc layer was washed with brine (100 mL), dried over Na ₂ SO _4, filtered and concentrated. The crude material was triturated with hexane, filtered and dried to give ((1- (2-aminopyridin-4-yl) piperidin-3-yl) methyl) aminocarboxylic acid tert-butyl ester 10-3 (2.5g , 52%), as an off-white solid, which was used in the next step without further purification. ESI + APCI-MS m / z 307 [M + H] ⁺ .

((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl) amino tert-butyl (tert -butyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-3-yl) methyl) carbamate) Preparation of 10-5

Tert-butyl ((1- (2-aminopyridin-4-yl) piperidin-3-yl) methyl) carbamate 10-3 (2.50 g, 8.1 mmol) and 2-bromo-1- (5-chloro-2,4-dimethoxyphenyl) ethanone 10-4 (2.62 g, 8.9 mmol) were heated for 16 hours. The reaction mixture was cooled to room temperature. The formed precipitate was collected by filtration, washed with hexane (100 mL) and dried. The hydrobromide was dissolved in water (50 mL) and a saturated sodium bicarbonate solution (100 mL), and stirred at room temperature for 1 hour. The solid was collected by filtration, washed with water and dried to give ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-3-yl) methyl) t-butylaminocarbamate 10-5 (3.10 g, 76%) as an off-white solid. ESI + APCI-MS m / z 501 [M + H] ⁺ .

(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) methylamine ((1- Preparation of (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-3-yl) methanamine) 10-6

((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine in CH ₂ Cl ₂ (30 mL) A solution of pyridin-3-yl) methyl) carbamic acid tert-butyl ester 10-5 (3.00 g, 6.0 mmol) was added to a solution of HCl (4.0 M in 1,4-dioxane, 30 mL), and The reaction mixture was stirred at warm for 16 hours. The resulting solid was collected by filtration and washed with CH ₂ Cl ₂ (100 mL). Then, the solid was suspended in water (70 mL), and stirred in a saturated sodium bicarbonate solution (70 mL) at room temperature for 1 hour. Filtration collected the precipitated off-white solid, washed with water and dried to give (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- Yl) piperidin-3-yl) methylamine 10-6 (1.60 g, 67%) as an off-white solid. ESI + APCI-MS m / z 401 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl yl) amino) methyl) pyrrolidine-1-carboxylate (tert -butyl 3 - ((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ) pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylate) 10-8a (Example 2-11)

For (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- in CH ₃ OH (5 mL)- 3-yl) methylamine 10-6 (100 mg, 0.25 mmol) and tert-butyl 3-methylpyrrolidine-1-carboxylic acid 10-7a, (74 mg, 0.37 mmol) solution, add acetic acid (0.1 mL), And the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (47 mg, 0.75 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate (20 mL), and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined were washed with brine (20mL) The organic extracts were dried over anhydrous Na ₂ SO _4, filtered and concentrated. The residue was purified by combi-rapid color chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to obtain 3-(((((1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) pyrrolidine-1 -Tert-butyl carboxylic acid 10-8a (20 mg, 14%) as an off-white solid.

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.30 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 8.00 (s, 1H), 6.86 (s, 1H), 6.78 (d, J = 7.6Hz, 1H), 6.69 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.82 (d, J = 11.6Hz, 1H), 3.71 (d, J = 11.6Hz, 1H), 3.45 (br s, 1H), 3.22-3.16 (m, 1H), 2.99-2.94 (m, 1H), 2.79-2.73 (m, 1H), 2.58-2.43 (m, 6H), 1.98-1.97 (m, 2H), 1.82-1.71 (m, 3H), 1.59-1.49 (m, 2H), 1.39 (s, 9H), 1.18-1.12 (m, 1H); HPLC (Method 4) 98.3% (Under the curve Area), t _R = 6.83 minutes; ESI + APCI-MS m / z 584 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) - N - ( Preparation of cyclohexylmethyl) methylamine 10-8b (Examples 2-20)

With 3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl ) Methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 10-8a The same method was used to prepare 1- (1- (2- (5-chloro-2) using cyclohexane formaldehyde 10-7b , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) - N - (cyclohexylmethyl) methanamine 10-8b, and off-white A solid was obtained (18% yield).

¹ H NMR (400MHz, DMSO- d ₆ , 362K): δ 8.19-8.16 (m, 2H), 7.91 (s, 1H), 6.84 (s, 1H), 6.66 (d, J = 8.0Hz, 1H), 6.60 (s, 1H), 3.98 (s, 3H), 3.91 (s, 3H), 3.70 (d, J = 13.2Hz, 1H), 3.60 (d, J = 11.6Hz, 1H), 2.86 (br s, 1H) 2.66-2.61 (m, 1H), 2.51-2.42 (m, 4H), 1.81-1.55 (m, 9H), 1.45-1.41 (m, 1H), 1.25-1.18 (m, 4H), 0.98-0.90 (m, 2H); HPLC (method 4) 98.7% (area under the curve), t _R = 6.85 minutes; ESI + APCI-MS m / z 497 [M + H] ⁺ .

3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl yl) amino) methyl) piperidine-1-carboxylate (tert -butyl 3 - ((( (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ) pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate) 10-8c (Example 2-76)

With 3-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl ) Methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester 10-8a (((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl) amine (Methyl) methyl) piperidine-1-carboxylic acid tert-butyl ester 10-8c and obtained as an off-white solid (9% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.29 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.77 (d, J = 7.2Hz, 1H), 6.68 (s, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.84-3.70 (m, 3H), 3.42-3.37 (m, 1H), 2.76 (t , J = 10.4Hz, 2H), 2.59-2.53 (m, 6H), 1.81-1.70 (m, 4H), 1.62-1.49 (m, 3H), 1.39 (s, 9H), 1.38-1.27 (m, 1H ), 1.17-1.11 (m, 2H); HPLC (Method 4) 94.3% (area under the curve), t _R = 6.91 minutes; ESI + APCI-MS m / z 598 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl Preparation of t-butylamino) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 11-3

For (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- in CH ₃ OH (5 mL)- 4-yl) methylamine 11-1 (150 mg, 0.37 mmol) and 4-formylpiperidine-1-carboxylic acid tert-butyl ester 11-2 (48 mg, 0.56 mmol) suspension, add acetic acid (0.1 mL), And the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (861 mg, 13.7 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate (100 mL), and the aqueous layer was extracted with CH ₂ Cl ₂ (2 × 50 mL). Washed with water and brine (50mL) The organic extracts were dried over anhydrous Na ₂ SO _4, filtered and concentrated. The residue was purified by combinatorial-fast chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to give 4-(((((1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidine-1 -Tert-butyl carboxylic acid 11-3 (550 mg, 33%) as an off-white solid. ESI + APCI-MS m / z 598 [M + H] ⁺ .

4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl ) ((2,2,2-trichloroethoxy) carbonyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl tert -butyl 4-((((1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4-yl) methyl) ((2,2,2-trichloroethoxy) carbonyl) amino) methyl) piperidine- Preparation of 1-carboxylate) 11-4

For 4-((((((1- (2- (2-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 in CH ₂ Cl ₂ (10 mL) -Yl) piperidine-4-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 11-3 (100 mg, 0.16 mmol) and Et ₃ N (0.07 mL, 0.50 mmol) solution , 2,2,2-trichloroethyl chloroformate (2,2,2-trichloroethyl carbonochloridate) (88 mg, 0.18 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with water and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined organic layers were dried over Na ₂ SO ₄ , filtered and concentrated to give 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) piperidin-4-yl) methyl) ((2,2,2-trichloroethoxy) carbonyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 11-4 (110 mg, raw) as an off-white solid. ESI + APCI-MS m / z 772 [M + H] ⁺ .

2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) methyl) (piperidin-4-ylmethyl) carbamate (2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo Preparation of [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) (piperidin-4-ylmethyl) carbamate) 11-5

For 4-((((((1- (2- (2-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 in CH ₂ Cl ₂ (10 mL) -Yl) piperidin-4-yl) methyl) ((2,2,2-trichloroethoxy) carbonyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester 11-4 (100 mg , 0.12 mmol), a solution of HCl (4.0 M in 1,4-dioxane, 1 mL) was added, and the reaction mixture was stirred at room temperature for 2 hours. The formed solid was collected by filtration, washed with CH ₂ Cl ₂ (10 mL) and dried. Then, the obtained hydrochloride was suspended in water (10 mL), and basified with a saturated sodium bicarbonate solution (10 mL) by stirring at ambient temperature for 1 hour. The yellow solid was collected by filtration, washed with water and dried to give 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) (piperidin-4-ylmethyl) carbamate 11-5 (45 mg, 52%) as an off-white solid . ESI + APCI-MS m / z 672 [M + H] ⁺ .

2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) methyl) ((1-neopentylpiperidin-4-yl) methyl) carbamate (2,2,2-trichloroethyl ((1- (2- (5-chloro- Preparation of 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) ((1-pivaloylpiperidin-4-yl) methyl) carbamate) 11-6a

Pair of CH ₂ Cl ₂ (5 mL) 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridine-7-yl) piperidin-4-yl) methyl) (piperidin-4-ylmethyl) carbamate 11-5 (50 mg, 0.07 mmol) solution, add (charge) new Pivaloyl chloride (0.01 mL, 0.08 mmol). The reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was diluted with water and extracted with CH ₂ Cl ₂ (2 × 10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) ((1-neopentylpiperidin-4-yl) methyl) carbamate 11-6a (55 mg, (Raw) as an off-white solid. ESI + APCI-MS m / z 756 [M + H] ⁺ .

1- (4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4- (Methyl) methyl) amino) methyl) piperidin-1-yl) -2,2-dimethylpropan-1-one 11-7a (Example 2-50)

For 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) in AcOH (1 mL) and H ₂ O (1 mL) [1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) ((1-neopentylpiperidin-4-yl) methyl) carbamate 11-6a (50mg , 0.06 mmol) suspension, Zn (10 mg) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude material was purified by combinatorial-rapid color chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to give 1- (4-(((((1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) piper Pyridin-1-yl) -2,2-dimethylpropan-1-one 11-7a (15 mg, 39%) as an off-white solid.

¹ H NMR (400MHz, CDCl ₃ ): δ 8.33 (s, 1H), 7.87 (d, J = 7.2Hz, 1H), 7.84 (s, 1H), 6.82 (d, J = 1.6Hz, 1H), 6.58 -6.56 (m, 2H), 4.42 (d, J = 12.4Hz, 2H), 3.99 (s, 3H), 3.95 (s, 3H), 3.74 (d, J = 12.4Hz, 2H), 2.81-2.73 ( m, 4H), 2.56-2.52 (m, 4H), 1.87-1.71 (m, 4H), 1.43-1.31 (m, 4H), 1.27 (s, 9H), 1.18-1.09 (m, 2H); HPLC ( Method 7) 95.2% (area under the curve), t _R = 6.73 minutes; ESI + APCI-MS m / z 582 [M + H] ⁺ .

2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) methyl) ((1-isobutylpiperidin-4-yl) methyl) carbamate (2,2,2-trichloroethyl ((1- (2- (5-chloro- Preparation of 2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4-yl) methyl) ((1-isobutylpiperidin-4-yl) methyl) carbamate) 11-6b

For 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] in DMF (2 mL) Pyridine-7-yl) piperidin-4-yl) methyl) (piperidin-4-ylmethyl) carbamate 11-5 (120 mg, 0.17 mmol) and K ₂ CO ₃ (73 mg, 0.53 mmol ) Suspension, 1-iodo-2-methylpropane (0.03 mL, 0.26 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with CH ₂ Cl ₂ (2 × 10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) ((1-isobutylpiperidin-4-yl) methyl) carbamate 11-6b (129 mg, (Raw) as an off-white solid. ESI + APCI-MS m / z 728 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( Preparation of (1-isobutylpiperidin-4-yl) methyl) methylamine 11-7b (Examples 2-60)

With 1- (4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- 4-yl) methyl) amino) methyl) piperidin-1-yl) -2,2-dimethylpropan-1-one 11-7a, 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -((1-isobutylpiperidine- 4-yl) methyl) methylamine 11-7b and obtained as an off-white solid (16% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.27 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.78 (dd, J = 2.4,8.0Hz, 1H), 6.62 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.79-3.76 (m, 2H), 2.78-2.64 (m , 4H), 2.44-2.37 (m, 4H), 1.97 (d, J = 7.6Hz, 2H), 1.80-1.70 (m, 5H), 1.67-1.57 (m, 3H), 1.41-1.31 (m, 1H ), 1.26-1.06 (m, 4H), 0.83 (d, J = 6.4 Hz, 6H); HPLC (method 7) 95.3% (area under the curve), t _R = 6.46 minutes; ESI + APCI-MS m / z 554 [M + H] ⁺ .

2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) methyl) ((1- (cyclobutylmethyl) piperidin-4-yl) methyl) carbamate (2,2,2-trichloroethyl ((1- (2- (5- chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4-yl) methyl) ((1- (cyclobutylmethyl) piperidin-4-yl) methyl) carbamate) 11-6c Preparation

For in CH ₃ OH (5mL) of 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) piperidin-4-yl) methyl) (piperidin-4-ylmethyl) carbamate 11-5 (250 mg, 0.36 mmol) and cyclobutanecarbaldehyde (37 mg, 0.44 mmol) of the suspension, acetic acid (0.1 mL) was added, and the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (43 mg, 1.82 mmol) was added in one portion, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture will be diluted with aqueous sodium bicarbonate solution (20 mL) and extracted with CH ₂ Cl ₂ (2 × 20 mL). The combined were washed with brine (20mL) The organic extracts were dried over anhydrous Na ₂ SO _4, filtered and concentrated. The crude material was purified by combinatorial-fast chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to obtain 2,2,2-trichloroethyl (( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) ((1- (Cyclobutylmethyl) piperidin-4-yl) methyl) carbamate 11-6c (220 mg, 80%) as an off-white solid. ESI + APCI-MS m / z 740 [M + H] ⁺ .

1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) - N - ( (1- (cyclobutylmethyl) piperidin-4-yl) methyl) methylamine (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin- 7-yl) piperidin-4-yl) -N -((1- (cyclobutylmethyl) piperidin-4-yl) methyl) methanamine) 11-7c (Example 2-80)

With 1- (4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- 4-yl) methyl) amino) methyl) piperidin-1-yl) -2,2-dimethylpropan-1-one 11-7a, 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -((1- (cyclobutylmethyl) piper Pyridin-4-yl) methyl) methylamine 11-7c and obtained as an off-white solid (13% yield).

¹ H NMR (400 MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6 Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.77 (dd, J = 2.4,7.6Hz, 1H), 6.62 (d, J = 2.0Hz, 1H), 4.00 (s, 3H), 3.93 (s, 3H), 3.77 (d, J = 12.4Hz, 2H), 2.72- 2.60 (m, 4H), 2.46-2.32 (m, 4H), 2.27 (d, J = 7.2Hz, 2H), 2.00-1.94 (m, 2H), 1.85-1.74 (m, 6H), 1.64-1.57 ( m, 5H), 1.31-1.11 (m, 4H), 1.09-1.06 (m, 2H); HPLC (method 4) 93.9% (area under the curve), t _R = 6.31 minutes; ESI + APCI-MS m / z 566 [M + H] ⁺ .

Scheme 17

4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Preparation of methyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester 11-10

1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 in CH ₃ OH (50 mL) -A suspension of formaldehyde 11-8 (1.0 g, 2.50 mmol) and 4- (2-aminoethyl) piperidine-1-carboxylic acid tert-butyl ester 11-9 (628 mg, 2.75 mmol) and acetic acid (0.5 mL) ), And the resulting mixture was stirred at room temperature for 2 hours. Sodium cyanoborohydride (788 mg, 12.53 mmol) was added, and the reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with aqueous sodium bicarbonate solution and extracted with CH ₂ Cl ₂ (2 × 100 mL). Dried over anhydrous Na ₂ SO ₄ the combined organic extracts were dried, filtered and concentrated. The crude material was purified by combinatorial-rapid color chromatography [silicone; 5% NH ₄ OH in MeOH: CH ₂ Cl ₂ (1: 9)] to obtain 4- (2-(((1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) ethyl) piperidine Tert-butyl-1-carboxylate 11-10 (480 mg, 73%) as an off-white solid.

¹ H NMR (400MHz, CD ₃ OD): δ 8.03 (d, J = 7.6Hz, 1H), 7.97 (s, 1H), 7.86 (s, 1H), 6.67 (dd, J = 5.2, 8.0Hz, 2H ), 6.57 (s, 1H), 3.98 (d, J = 8.4Hz, 2H), 3.92 (s, 3H), 3.85 (s, 3H), 3.76 (d, J = 12.8Hz, 2H), 2.74-2.59 (m, 6H), 2.48 (d, J = 6.8Hz, 2H), 1.79 (d, J = 12.8Hz, 2H), 1.60 (d, J = 12.8Hz, 3H), 1.43-1.39 (m, 2H) , 1.35 (s, 9H), 1.28-1.21 (m, 3H), 1.03-0.98 (m, 2H); ESI + APCI MS m / z 612 [M + H] ⁺ .

4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) Methyl) ((2,2,2-trichloroethoxy) carbonyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl tert -butyl 4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4-yl) methyl) ((2,2,2-trichloroethoxy) carbonyl) amino) Preparation of ethyl) piperidine-1-carboxylate) 11-11

4- (2-(((1- (2- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine in CH ₂ Cl ₂ (25 mL) -7-yl) piperidin-4-yl) methyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester 11-10 (500 mg, 0.81 mmol) and Et ₃ N (0.35 mL, 2.44 mmol ) Solution, 2,2,2-trichloroethyl chloroformate (190 mg, 0.89 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water, and extracted with _{CH 2 Cl 2 (2 × 50mL} ). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give 4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a) pyridine-7-yl) piperidin-4-yl) methyl) ((2,2,2-trichloroethoxy) carbonyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl Ester 11-11 (450 mg, raw) as an off-white solid. ESI + APCI-MS m / z 786 [M + H] ⁺ .

2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) methyl) (2- (piperidin-4-yl) ethyl) carbamate (2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4 -dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4-yl) methyl) (2- (piperidin-4-yl) ethyl) carbamate) 11-12

4- (2-(((1- (2- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine in CH ₂ Cl ₂ (50 mL) -7-yl) piperidin-4-yl) methyl) ((2,2,2-trichloroethoxy) carbonyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester 11-11 (600 mg, 0.77 mmol) solution, HCl solution (4.0 M, 2 mL) in 1,4-dioxane was added, and the reaction mixture was stirred at room temperature for 2 hours. The formed solid was collected by filtration, washed with CH ₂ Cl ₂ and dried. Then, the obtained hydrochloride was suspended in water (10 mL), and basified with a saturated sodium bicarbonate solution (10 mL) by stirring at room temperature for 1 hour. The pale yellow solid was collected by filtration, washed with water and dried to give 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxybenzene) (Yl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) (2- (piperidin-4-yl) ethyl) carbamate 11-12 ( 400 mg, 76%) as an off-white solid. ESI + APCI-MS m / z 686 [M + H] ⁺ .

2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) methyl) (2- (1-neopentylpiperidin-4-yl) ethyl) carbamate (2,2,2-trichloroethyl ((1- (2- (5- chloro-2,4-dimethoxyphenyl) imidazo [1,2- a ] pyridin-7-yl) piperidin-4-yl) methyl) (2- (1-pivaloylpiperidin-4-yl) ethyl) carbamate) 11-13 preparation

Pair of CH ₂ Cl ₂ (10 mL) 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridine-7-yl) piperidin-4-yl) methyl) (2- (piperidin-4-yl) ethyl) carbamate 11-12 (100 mg, 0.14 mmol) solution, added Neopentyl chloride (0.02 mL, 0.16 mmol). The reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was diluted with water and extracted with CH ₂ Cl ₂ (2 × 10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give 2,2,2-trichloroethyl ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) (2- (1-neopentylpiperidin-4-yl) ethyl) carbamate 11-13 ( 110 mg, raw) as an off-white solid. ESI + APCI-MS m / z 770 [M + H] ⁺ .

1- (4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- Preparation of 4-yl) methyl) amino) ethyl) piperidin-1-yl) -2,2-dimethylpropan-1-one 11-14 (Example 2-69)

With 1- (4-((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- 4-yl) methyl) amino) methyl) piperidin-1-yl) -2,2-dimethylpropan-1-one 11-7a The same method was used to prepare 1- (4- (2- ( ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino ) Ethyl) piperidin-1-yl) -2,2-dimethylpropan-1-one 11-14 and obtained as an off-white solid (14% yield).

¹ H NMR (400MHz, DMSO- d ₆ ): δ 8.26 (d, J = 7.6Hz, 1H), 8.16 (s, 1H), 7.99 (s, 1H), 6.86 (s, 1H), 6.77 (dd, J = 2.0, 7.6 Hz, 1H), 6.62 (d, J = 1.6 Hz, 1H), 4.24 (d, J = 12.8 Hz, 2H), 4.00 (s, 3H), 3.93 (s, 3H), 3.78 ( d, J = 13.2Hz, 2H), 2.73-2.67 (m, 4H), 2.40 (d, J = 6.4Hz, 2H), 1.79 (d, J = 11.2Hz, 2H), 1.67-1.56 (m, 5H ), 1.36-1.31 (m, 2H), 1.25-1.18 (m, 3H), 1.17 (s, 9H), 1.01-0.91 (m, 2H); ESI + APCI-MS m / z 596 [M + H] ⁺ .

The compounds of the present invention, which are not specifically described in the above examples, can also be synthesized by similar or similar methods, and by referring to the above examples and the like.

Next, the pharmacological activity of the compound (I) will be described in the following test examples.

Preparation of compound dilution plate (96-well plate)

100% DMSO was added to the test compound to obtain a stock solution with a final concentration of 10 mM, and the solution was incubated overnight at 150 rpm on a shaker. In a 96-well plate, dispense 75 μL of 50% DMSO (in water) to all wells from column 3 (Col 3.) to column 11. (Row A) to H). 24 μL of a 10 mM compound stock was added to column 2 (rows A to H) to give a final concentration of 2.4 mM. The mixture (25 μl) in each well in column 2 was mixed and transferred to the corresponding well in column 3. Similar steps were repeated until column 11 to obtain 10 serial dilutions of each compound (1: 4).

Preparation of standard compound plate (96-well plate)

Add assay buffer (18 μl) to columns A in columns 3 to 11, and add Sinefungin (24 μl, 12.5 mM) to column 2. The mixture from row A-column 2 (6 μl) was transferred to the corresponding well in column 3. The mixture (24 μl) in the wells of column 3 was mixed and transferred to column 4, and similar steps were continued up to column 11 to obtain a 10-point serial dilution of sinefendin.

Preparation of 384-well test plate

Add water (0.25 μl) to columns 1 and 23 (minimum and maximum signal holes, respectively), and add 50% DMSO (0.25 μl) to columns 2 and 24 (minimum and maximum signals, respectively) hole). The test compound (0.25 l) was added to each well in the "rows A to N". "O" contains internal standard compounds. Xinafine (4 μl) was added to “P rows”. Each compound concentration was tested in duplicate.

Suv 39H2 determination

Multidrop Combi was used to add assay buffer (4 μL) to all wells, including the test compound and control wells (except for the xinafine net control wells). Centrifuge the plate at 1000 rpm for 1 minute. Using Multidrop Combi, a matrix mixture (8 μL) containing radiolabeled ³ H-SAM (final concentration: 100 nM) and H3 histone peptide (final concentration: 350 nM) was added to all wells and centrifuged at 1000 rpm 1 minute. By using Multidrop Combi, SUV39H2 (8 μL, final concentration: optimized for each batch of enzymes based on specific activity) was added. Centrifuge the assay disk at 1000 rpm for 1 minute. The assay buffer was used as a background control and incubated for 3 hours at room temperature. Using Multidrop Combi, the reaction was stopped with 20 μL of 2.5 mg / mL Streptavidin SPA beads (final concentration 50 μg / well) in buffer and centrifuged for 1 minute. The disc was loaded into a Trilux-Microbeta counter and the delayed read was 10 hours. The radioactive signal is measured at 1 minute / well. Cinafinide and internal standard compounds were used as tool compounds to determine assay potency.

data analysis

˙Using the obtained CPM raw data, perform the following calculations: Software used: XLFit from IDBS. The model used was-DoseResponse One Site-model 205.

˙1% DMSO / water negative control (minimum signal-columns 1 and 2) = average of all background control wells.

˙1% DMSO / water positive control (maximum signal-columns 23 and 24) = average of all control wells.

˙Signal ratio = (positive control) / (negative control).

˙Z '= 1-(((3 * standard deviation of negative control) + (3 * standard deviation of positive control)) / (mean of positive control-mean of negative control)).

%% Inhibition of test compound = (100-((average of CPM _{test compound} -average of CPM _{negative control} ) / (average of CPM _{positive control} -average of CPM _{negative control} )) x 100).

For each test disc, calculate the following results:

˙ Mean, standard deviation and coefficient of variation (CV)% of background control.

˙ Mean, standard deviation and coefficient of variation (CV)% of positive control.

˙Z 'value of the plate.

˙ IC ₅₀ values (in nM) for standard and test compounds.

˙ Fit the R ² value of the fitted concentration response curve.

˙Hill slope coefficient of fitted concentration response curve.

˙Signal to noise ratio.

For each sample compound, describe the following results:

ConConcentration dependent response curve for each compound.

Concentrations of osmium compounds that cause 50% inhibition of enzyme activity (IC ₅₀ value (nM)).

%% Inhibition at the maximum concentration tested.

˙ Maximum concentration tested.

˙ Fit the R ² value of the concentration response curve.

˙Hill slope coefficient of fitted concentration response curve.

The IC ₅₀ values of typical compounds of the invention are shown in Table 3 below:

Western blot analysis

To assess the performance status of SUV39H2 in several cell lines, crude ink lysates collected from those cells were used for Western blot analysis. Anti-SUV39H2 antibodies were used to visualize performance. The cancer cell lines A549, HCT-116, HFL1, CCD-18Co, and PC14 showed significant SUV39H2.

Cell-based assay

Using A549, target-specific cytotoxicity against candidate inhibitors of activity against SUV39H2 was evaluated. 100 microliters (micro-L) of the cell suspension was seeded on a 96-well microtiter plate (ViewPlate-96FTC, PerkinElmer). The initial cell concentrations of A549 were 3,000 cells / well, 2,000 cells / well, and 2,500 cells / well, respectively. 72 hours after the exposure of the candidate inhibitors, cell growth was measured using Cell Counting Kit-8 (DOJINDO). IC ₅₀ activity as an anti-proliferative index inhibitors, and methods by dilution sequence (0,1.5625,3.125,6.25,12.5,25,50 and 100 micro-M) is calculated. The exact IC ₅₀ value is calculated in the aforementioned manner.

IC ₅₀ values of typical compounds of the present invention (Examples 1 to 68) are shown in the following Tables 3-1 and 3-2:

Claims (16)

A compound represented by formula (I) or a pharmaceutically acceptable salt thereof: Wherein R ¹ and R ^{2 are} independently selected from the group consisting of halogen atom, hydroxy, C ₁ -C ₆ alkyl and C ₁ -C ₆ alkoxy; R ^{3 is} independently selected from halogen Atom, cyano, nitro, hydroxyl, carboxyl, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, (C ₁ -C ₆ alkoxy) carbonyl ( carbonyl), C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl and C ₁ -C ₆ alkylsulfonyl; n Is an integer selected from 0 to 3; R ⁴ is selected from the group consisting of a hydrogen atom and a halogen atom; R ^{5 is} independently selected from the group consisting of a halogen atom, a C ₁ -C ₆ alkyl group, and a C ₁ -C ₆ alkoxy group A group consisting of; m is an integer selected from 0 to 3; X and Y are independently selected from a direct bond, -CH ₂ -and -CH ₂ CH _2- ; R ^{6 is} selected from one or more selected from Ra C ₁ -C ₆ alkyl substituted with a substituent, C ₃ -C ₁₀ cycloalkyl optionally substituted with one or more substituents selected from Rb, optionally substituted with one or more selected from 5-10, optionally substituted with one or more substituents selected from Rb and Rb substituents C ₆ -C ₁₀ aromatic group (and aryl) substituted heteroaryl selected from Heteroaryl, 3 to 12-membered non-aromatic heterocyclyl optionally substituted with one or more substituents selected from Rb, substituted with one or more substituents selected from Ra the (C ₁ -C ₆ alkoxy) carbonyl group, by one or more substituents selected from Ra substituted (C ₁ -C ₆ alkyl) carbonyl group, substituted with one or more substituents selected from the group Rc, (C ₃ -C ₁₀ cycloalkyl) carbonyl, (C ₆ -C ₁₀ aryl) carbonyl substituted with one or more substituents selected from Rd, ( 3- to 12-membered non-aromatic heterocyclic) carbonyl, (5- to 10-membered heteroaryl) carbonyl substituted with one or more substituents selected from Rc, aminocarbonyl, (C ₁ -C ₆ A group consisting of alkyl) aminocarbonyl and di (C ₁ -C ₆ alkyl) aminocarbonyl; R ^{7 is} selected from C substituted by a hydrogen atom and optionally substituted by one or more substituents selected from Ra ₁ -C ₆ alkyl group; Q is selected from C ₁ -C ₆ alkylene; R ^{10 is} independently selected from group consisting of halogen atom and C ₁ -C ₆ alkyl group; q Is an integer selected from 0 to 4; Ra is independently selected from a halogen atom, a hydroxyl group, a C ₁ -C ₆ alkoxy group , Cyano, (C ₁ -C ₆ alkoxy) carbonyl, carboxyl, (C ₁ -C ₆ alkoxy) carbonylamino, (C ₁ -C ₆ alkyl) carbonylamino, amine , C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, aminocarbonyl, (C ₁ -C ₆ alkyl) aminocarbonyl, di (C _1- C ₆ alkyl) aminocarbonyl, C ₁ -C ₆ alkylsulfonylamino, C ₃ -C ₁₀ cycloalkylsulfonylamino, optionally Rc is selected from a plurality of substituents of C ₃ -C ₁₀ cycloalkyl, optionally substituted with C ₃ -C ₁₀ cycloalkenyl group (cycloalkenyl), optionally substituted with one or more substituents selected from Rc, C ₆ -C ₁₀ aromatic groups substituted with one or more substituents selected from Rd, 5- to 10-membered heteroaryl groups optionally substituted with one or more substituents selected from Rc, and optionally Or a group of 4 to 12 membered non-aromatic heterocyclic groups substituted with a substituent selected from Rc; Rb is independently selected from a halogen atom, a hydroxyl group, and optionally substituted with one or more substituents selected from Ra substituted C ₁ -C ₆ alkyl, optionally substituted by one or more substituents selected from Ra, Substituted C ₁ -C ₆ alkoxy, cyano, (C ₁ -C ₆ alkoxy) carbonyl group, a carboxyl ^{group, -NR 21 R 22, -CONR 23} R 24, two (C ₁ -C ₆ alkyl) , optionally substituted with one or more substituents of C ₃ -C ₁₀ cycloalkyl, acyl phosphine (phosphono) Rc is selected, optionally substituted with one or more substituents selected from Rd is C ₆ -C ₁₀ aryl, 5 to 10 membered heteroaromatic groups optionally substituted with one or more substituents selected from Rc, and 3 to 12 members optionally substituted with one or more substituents selected from Rc A group consisting of non-aromatic heterocyclic groups; Rc is independently selected from a C ₁ -C ₆ alkyl group optionally substituted with one or more halogen atoms, optionally substituted with one or more halogen atoms, Halogen-substituted C ₁ -C ₆ alkoxy, halogen atom, amine, cyano, C ₁ -C ₆ alkylamino, bis (C ₁ -C ₆ alkyl) amino, (C ₁ -C ₆ alkyl) carbonyl, (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ alkylsulfonyl, C ₃ -C ₁₀ cycloalkylsulfonyl, optionally one or more selected since Re substituents substituted C ₇ -C _14, optionally substituted with one or more substituents selected from Re aralkyl (aralkyl) a C ₆ -C ₁₀ Hong group, optionally substituted with one or more substituents selected from Re, substituted C ₃ -C ₁₀ cycloalkyl, optionally substituted with one or more substituents selected from Re, 3 to 12 membered non-aromatic A heterocyclic group, a 5- to 10-membered heteroaryl group optionally substituted with one or more substituents selected from Re and an oxo group; Rd is independently selected from the group consisting of nitro, hydroxyl , optionally substituted with one or more halogen atoms substituted C ₁ -C ₆ alkyl, optionally substituted with one or more halogen atoms substituted C ₁ -C ₆ alkoxy group, a halogen atom, an amine group, a cyano group , C ₁ -C ₆ alkylamino, di (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkylcarbonyl, (C ₁ -C ₆ alkoxy) carbonyl, C ₁ -C ₆ Alkylsulfonyl, C ₃ -C ₈ cycloalkylsulfonyl, C ₇ -C ₁₄ aralkyl optionally substituted with one or more substituents selected from Re, optionally via one or more C ₆ -C ₁₀ aromatic groups substituted with a substituent selected from Re, C ₃ -C ₈ cycloalkyl optionally substituted with one or more substituents selected from Re, optionally with one or more 3- to 12-membered non-aromatic heterocyclic groups substituted with a substituent selected from Re and optionally one or more selected from Re A group of 5 to 10 membered heteroaryl groups substituted by a substituent; Re is independently selected from a C ₁ -C ₆ alkyl group, a halogen atom, a nitro group, a hydroxyl group, optionally substituted with one or more halogen atoms, Amino, cyano, C ₁ -C ₆ alkylamino, bis (C ₁ -C ₆ alkyl) amino, C ₁ -C ₆ alkylcarbonyl, (C ₁ -C ₆ alkoxy) carbonyl, A group consisting of C ₁ -C ₆ alkylsulfonyl and C ₃ -C ₈ cycloalkylsulfonyl; R ^{21 is} selected from a hydrogen atom, optionally substituted with one or more substituents selected from Ra C ₁ -C ₆ alkyl, C ₆ -C ₁₀ aromatic optionally substituted with one or more substituents selected from Rd, 4 optionally substituted with one or more substituents selected from Rd To 12-membered heterocyclyl, 5 to 10-membered heteroaryl optionally substituted with one or more substituents selected from Rc, (C ₁ -C ₆ alkoxy) carbonyl, (C ₁ -C ₆ alkyl) carbonyl, (C ₃ -C ₁₀ cycloalkyl) carbonyl, optionally substituted with one or more substituents selected from Ra, selectivity (C ₆ -C ₁₀ aryl) carbonyl substituted with one or more substituents selected from Rd, optionally with one or more (3- to 12-membered non-aromatic heterocyclic) carbonyl substituted with a substituent selected from Rc, (5- to 10-membered heteroaromatic) carbonyl optionally substituted with one or more substituents selected from Rc, Aminocarbonyl, (C ₁ -C ₆ alkyl) aminocarbonyl optionally substituted with one or more substituents selected from Ra, disubstituted optionally with one or more substituents selected from Ra (C ₁ -C ₆ alkyl) aminocarbonyl, optionally substituted with one or more halogen atoms substituted C ₁ -C ₆ alkylsulfonyl group, C ₇ -C ₁₄ aralkyl alkylsulfonyl group, C ₃ -C ₁₀ cycloalkylsulfonyl, aminesulfonyl, C ₁ -C ₆ alkylaminosulfonyl, di (C ₁ -C ₆ alkyl) aminosulfonyl and di (C _1- A group consisting of C ₆ alkyl) phosphonium groups; R ^{22 is} selected from the group consisting of a hydrogen atom and a C ₁ -C ₆ alkyl group optionally substituted with one or more substituents selected from Ra; R ^{23 is} selected from the group consisting of a C ₁ -C ₆ alkyl group optionally substituted with a hydrogen atom, optionally substituted with one or more substituents selected from Ra, [(C _1- C ₆ alkyl) amino] C ₁ -C ₆ alkyl, [di (C ₁ -C ₆ , optionally substituted with one or more substituents selected from Ra Alkyl) amino] C ₁ -C ₆ alkyl, C ₃ -C ₁₀ cycloalkyl optionally substituted with one or more substituents selected from Rc, optionally via one or more selected from Rd A C ₆ -C ₁₀ aromatic group substituted with 5 to 10 membered heteroaryl groups optionally substituted with one or more substituents selected from Rc, and optionally substituted with one or more substituents selected from Rc A group consisting of 3 to 12 membered non-aromatic heterocyclic groups substituted with an alkyl group; and R ^{24 is} selected from a C ₁ -C ₆ alkyl group substituted with a hydrogen atom and optionally substituted with one or more substituents selected from Ra A group of people. The compound or a pharmaceutically acceptable salt thereof according to item 1 of the scope of patent application, wherein R ⁷ is a hydrogen atom. The compound or pharmaceutically acceptable salt thereof according to item 1 or 2 of the scope of patent application, wherein R ^{6 is} selected from a pyrimidyl group, optionally a halogen atom, or a C ₁ -C ₆ alkoxy group Substituted pyridyl, piperidyl optionally substituted with a C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group, optionally with C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group substituted pyrrolidyl, optionally with a di (C ₁ -C ₆ alkyl) amino group or C _1- C ₆ alkyl group substituted C3-C ₇ cycloalkyl, tetrahydrofuryl, tetrahydropyranyl, phenyl optionally substituted by a substituent selected from Rb The group consisting of a group -CH ₂ -Ra, a group -CH ₂ CH ₂ -Ra, and a group -CH ₂ CH ₂ CH ₂ -Ra. According to the compound described in any one of claims 1 to 3 or a pharmaceutically acceptable salt thereof, Ra is independently selected from the group consisting of a hydroxyl group, a C ₁ -C ₆ alkoxy group, and optionally a di (C _1- C ₆ alkyl) amino-substituted C ₃ -C ₇ cycloalkyl, phenyl optionally substituted with one or more substituents selected from Rd, optionally C ₁ -C ₆ Pyrrolidinyl substituted with an alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group, optionally with a C ₁ -C ₆ alkyl group or (C ₁ -C ₆ alkoxy) carbonyl group Group substituted piperidinyl, optionally substituted with halogen atom or C ₁ -C ₆ alkoxy group, pyridyl, thiazolyl, thienyl, optionally through di (C ₁ -C ₆ alkyl) amino group substituted pyrimidinyl and C ₃ -C ₇ cycloalkenyl group.     According to the compound described in any one of claims 1 to 4 or a pharmaceutically acceptable salt thereof, Rb and Rd are independently selected from the group consisting of a halogen atom, a methyl group, and a cyano dimethylamino group. ), Methoxy, nitro, hydroxy, and trifluoromethyl.     The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 5, wherein the compound is represented by formula (Ib): Q is selected from -CH _2- , -CH (CH ₃ )-, -CH (CH ₂ CH ₃ )-, -CH ₂ CH _2- , -CH (CH ₃ ) CH _2- , and -CH ₂ CH (CH ₃ )-The group formed; R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , X, Y, m and n are any of the items 1 to 5 of the scope of patent application As defined. The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 6 of the scope of patent application, wherein X and Y are-(CH ₂ )-, X and Y are direct bonds, Or X is a direct bond and Y is-(CH ₂ )-. The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 7, wherein the compound is represented by formula (Ic): Wherein R ¹ and R ^{2 are} independently selected from the group consisting of C ₁ -C ₆ alkoxy groups, p is an integer selected from 0 and 1; R ³ is selected from the group consisting of halogen atoms, and R ⁶ And R ⁷ are defined by any one of claims 1 to 6 of the scope of patent application. The compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 7, wherein R ¹ and R ² are methoxy groups, and R ³ is a chlorine atom. The compound or a pharmaceutically acceptable salt thereof according to item 1 of the scope of patent application, which is selected from the group consisting of 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopropylmethyl) methylamine (1- (1- (2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopropylmethyl) methanamine); 1- (1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopentylmethyl) methylamine (1- (1 -(2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclopentylmethyl) methanamine); 3-((((( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl Tert-Butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin-7- yl) piperidin-4-yl) methyl) amino) methyl) pyrrolidine-1-carboxylate); 3-((((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) (methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl tert-butyl 3- ( ( ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) (methyl) amino) methyl) pyrrolidine-1 -carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (pyrrolidin-3-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin -4-yl) -N- (pyrrolidin-3-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridin-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) methanamine); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl 4-(( ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidine-1-carboxylate) ; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (Piperidin-4-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dim ethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (piperidin-4-ylmethyl) methanamine); N-benzyl-1- (1- (2- (5 ( -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methylamine (N-Benzyl-1- (1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methanamine); 1- (1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methylbenzyl ) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4- methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) -N- (2-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4 -yl) -N- (2-fluorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) piperidin-4-yl) -N- (3-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl ) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (3-fluorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-di (Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluorobenzyl) methylamine (1- (1- (2- ( 5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluorobenzyl) methanamine); 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxybenzyl) methyl Amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxybenzyl) methanamine ); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N -(2-chlorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-chlorobenzyl) methanamine); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylaniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylaniline); 3-(((((1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile (3-((( (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile); 4-(( ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino ) Methyl) benzonitrile (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) benzonitrile); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine -4-yl) -N- (2-nitrobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7- yl) piperidin-4-yl) -N- (2-nitrobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) piperidin-4-yl) -N- (3- (trifluoromethyl) benzyl) methylamine (1- (1- (2- (5-Chloro-2,4- dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (3- (trifluoromethyl) benzyl) methanamine) ; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (Pyridine-3-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl ) -N- (pyridin-3-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) piperidin-4-yl) -N- (pyridin-4-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-4-yl) -N- (pyridin-4-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((3-fluoropyridin-4-yl) methyl) methylamine (1- (1- (2 -(5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((3-fluoropyridin-4-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( (2-methoxypyridin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl ) piperidin-4-yl) -N-((2-methoxypyridin-4-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazole Benzo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) methanamine); 1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) (1- ( 1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thiazol-2-ylmethyl) methanamine); 1 -(1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N, N- Bis (pyridin-2-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4- yl) -N, N-bis (pyridin-2-ylmethyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) piperidin-4-yl) methyl) cyclobutylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cyclobutanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) piperidin-4-yl) methyl) cyclopentylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cyclopentanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) piperidin-4-yl) methyl) tetrahydrofuran-3-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] pyridin-7-yl) piperidin-4-yl) methyl) tetrahydrofuran-3-amine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) cyclohexylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) methyl) cyclohexanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) piperidin-4-yl) methyl) tetrahydro-2H-pyran-4-amine (N-((1- (2- (5-Chloro-2,4 -dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) tetrahydro-2H-pyran-4-amine); N-((1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cycloheptylamine (N-((1- (2- ( 5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) cycloheptanamine); N-((1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) Methyl) -1-methylpiperidine-4-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin -4-yl) methyl) -1-methylpiperidin-4-amine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) piperidin-4-yl) methyl) -1-isopropylpiperidin-4-amine (N-((l- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -1-isopropylpiperidin-4-amine); 1- (1- (2- (5-chloro-2,4-di (Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-methylpiperidin-4-yl) methyl) methylamine ( 1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-methylpiperidin-4- yl) methyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine- 4-yl) methyl) -2- (1-methylpiperidin-4-yl) ethylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (1-methylpiperidin-4-yl) ethanamine); N1-((1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -N ⁴ , N ⁴ -Dimethylcyclohexane-1,4-diamine (N1-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin -4-yl) methyl) -N4, N4-dimethylcyclohexane-1,4-diamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a) pyridine-7-yl) pyrrolidin-3-yl) -N- (cyclopropylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cyclopropylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxybenzene) Yl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cyclopentylmethyl) methylamine (1- (1- (2- (5-Chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cyclopentylmethyl) methanamine); 3-((((((1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid Tert-Butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl ) amino) methyl) pyrrolidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Pyrrolidin-3-yl) -N- (pyrrolidin-3-yl (Methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyrrolidin- 3-ylmethyl) methanamine); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrole Alkyl-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl ) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (piperidin-4-ylmethyl) methylamine (1- (1 -(2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (piperidin-4-ylmethyl) methanamine); N- Benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) formyl Amine (N-Benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2- Fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-fluorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (3-fluorobenzyl) methylamine (1-()-(2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (3-fluorobenzyl) methanamine); 1- (1- (2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-fluorobenzyl) methanamine); 4- ((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) (Amino) methyl) -N, N-dimethylaniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin-7- yl) pyrrolidin-3- yl) methyl) amino) methyl) -N, N-dimethylaniline); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazole Benzo [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) phenol (4-(((((1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) phenol); 1- ( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-nitro Benzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- ( 2-nitrobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3 -Yl) -N- (3- (trifluoromethyl) benzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin- 7-yl) pyrrolidin-3-yl) -N- (3- (trifluoromethyl) benzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) pyrrolidin-3-yl) -N- (4- (trifluoromethyl) benzyl) methylamine (1- (1- (2- (5-Chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4- (trifluoromethyl) benzyl) methanamine); 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-methylbenzyl) methanamine) ; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyridine Pyridine-3-yl) -N- (2-chlorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7 -yl) pyrrolidin-3-yl)-N- (2-chlorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridine-7-yl) pyrrolidin-3-yl) -N- (4-chlorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-chlorobenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyridin-3-ylmethyl) methylamine (1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyridin-3-ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyridin-4-ylmethyl) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (pyridin-4- ylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) -N-((3-fluoropyridin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imida zo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((3-fluoropyridin-4-yl) methyl) methanamine); 1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((2-fluoropyridin-4-yl) methyl ) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((2- fluoropyridin-4-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidin-3-yl) -N, N-bis (pyridin-2-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) pyrrolidin-3-yl)-N, N-bis (pyridin-2-ylmethyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethyl) Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-methoxyethylamine (N-((1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-methoxyethanamine); N-((1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cyclobutylamine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cyclobuta namine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) Methyl) -1-methylpiperidine-4-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin -3-yl) methyl) -1-methylpiperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) pyrrolidin-3-yl) -N-((1-methylpiperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpiperidin-4-yl) methyl) methanamine); N-((1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) aniline (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) aniline); N-((1- (2- (5 (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-phenylethyl-1-amine ( N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-phenylethan-1-amine ); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (thien-2-ylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin- 4-yl) -N- (thiophen-2-ylmethyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) pyrrolidin-3-yl) methyl) -2- (1-methylpiperidin-4-yl) ethyl-1-amine (N-((1- (2- (5- ( Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2- (1-methylpiperidin-4-yl) ethan-1-amine); N -Benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine-3 -Methylamine (N-Benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methanamine ); 4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine-4 -Yl) methyl) amino) ethyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) ethyl) piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (4-fluorobenzyl) methyl (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (4-fluorobenzyl) methanamine) ; 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine-3 -Yl) methyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) pyrrolidine-1-carboxylate); 4-(((((1- (2- (5-chloro-2,4 -Dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid Tert-Butyl 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) -methyl) piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) azetidin-3-yl) -N- (cyclopentylmethyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) azetidin-3-yl) -N- (cyclopentylmethyl) -methanamine); 4- (2-(((1- (2- (5-chloro-2,4-dimethylformamide) Oxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- ) Methyl) amino) ethyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo -[1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) ethyl) -piperidine-1-carboxylate); 3-(((((1- (2- (5-chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) -pyrrolidine-1-carboxylic acid Tert-Butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) -pyrrolidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) -N- (1-isopropylpiperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl ) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-isopropylpiperidin-4-yl) methyl) methanamine); 2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline (2-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3- yl) methyl ) amino) methyl) -N, N-dimethylaniline); 1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2,4-dimethoxybenzyl ) -Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2, 4-dimethoxybenzyl) -methanamine); 2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylaniline (2-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylaniline); 1- (1- (2- (5-chloro-2,4-di (Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (cyclohexylmethyl) methylamine (1- (1- (2 -(5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (cyclohexylmethyl) methanamine); 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxy-2-nitro Benzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- ( 4-methoxy-2-nitrobenzyl) methanamine); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a) pyridine-7-yl) azetidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline (4-((((1- ( 2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline); 5- ( (((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amine (Methyl) methyl) -2-methoxyphenol (5-((((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin-7-yl) piperidin -4-yl) methyl) amino) methyl) -2-methoxyphenol); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) piperidin-3-yl) -N- (cyclohexylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-3-yl) -N- (cyclohexylmethyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a] pyridine-7-yl) pyrrolidin-3-yl) -N- (4-fluoro-3-methylbenzyl) -methylamine (1- (1- (2- (5-Chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (4-fluoro-3-methylbenzyl) -methanamine); 1- (1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- ) -N- (4-methoxy-3-methylbenzyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin -7-yl) pyrrolidin-3-yl) -N- (4-methoxy-3-methylbenzyl) -methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-fluoro-4-methylbenzyl) methylamine (1- (1- (2- ( 5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-fluoro-4-methylbenzyl) methanamine); N ¹ -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl)- N ⁴ , N ⁴ -Dimethylcyclohexane-1,4-diamine (N ¹ -((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -N ⁴ , N ⁴ -dimethylcyclohexane-1,4-diamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrole Alk-3-yl) -N- (3-fluoro-4-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] pyridin-7-yl) pyrrolidin-3-yl)-N- (3-fluoro-4-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxybenzene Yl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2,4-difluorobenzyl) methylamine (1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2,4-difluorobenzyl) methanamine; N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-isopropylpiperidine- 4-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-isopropylpiperidin -4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- ) -N-((1-ethylpiperidin-4-yl) methyl) propan-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a) pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) propan-1-amine) 1- (tert-butyl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) piper Pyridin-4-yl) methyl) piperidin-4-amine (1- (tert-Butyl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2 -a] pyridin-7-yl) piperidin-4-yl) methyl) piperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) piperidin-4-yl) -N-((1-ethylpiperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-ethylpiperidin-4-yl) methyl) methanamine); N -((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl)- 2- (1-ethylpiperidin-pyridin-4-yl) ethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (1-ethylpiperidin-4-yl) ethan-1-amine); N-((1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cycloheptylamine (N-((1- (2- (5-Chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) cycloheptanamine); N-((1- (2- (5-chloro-2,4- Dimethoxybenzene ) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-ethylpiperidin-4-amine (N-((1- (2- (5- ( Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -1-ethylpiperidin-4-amine); 1- (1- (2- (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2,4-dimethoxybenzyl ) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2,4 -dimethoxybenzyl) methanamine); 1- (tert-butyl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) pyrrolidin-3-yl) methyl) piperidine-4-amine (1- (tert-Butyl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [l, 2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) piperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxybenzene) Yl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) methylamine (1- (1 -(2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piper -4-yl) methyl) -2-cyclopentylethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin- 7-yl) piperidin-4-yl) methyl) -2-cyclopentylethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) azetidin-3-yl) -N- (2-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (2-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxy-3-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-methoxy-3- methylbenzyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidine -3-yl) methyl) -3,3-dimethylbut-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) -3,3-dimethylbutan-1-amine); 2-(((((1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -5-methoxyphenol (2-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -5-methoxyphenol); 5-(((((1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl ) -2-methoxyphenol (5-((((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) methyl) amino) methyl) -2-methoxyphenol); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- ) Azetidin-3-yl) -N- (4-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a] pyridin-7-yl) azetidin-3-yl) -N-(4-methylbenzyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2- (1-propylpiperidin-4-yl) ethyl-1-amine (N- ( (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2- (1-propylpiperidin-4-yl ) ethan-1-amine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine -3-yl) methyl) -2- (1-ethylpiperidin-4-yl) ethyl-1-amine (N-((1- (2- (5-Chloro-2,4-d imethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2- (1-ethylpiperidin-4-yl) ethan-1-amine); 1- (1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-methylpyrrolidine -3-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-methylpyrrolidin-3-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) piperidin-4-yl) -N-((1-ethylpiperidin-3-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-ethylpiperidin-3-yl) methyl) methanamine); 3-(((((1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl Tert-Butyl 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a) pyridin-7- yl) pyrrolidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a) pyridine-7-yl) pyrrolidin-3-yl) -N- (cycloheptylmethyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl)-N- (cycloheptylmethyl) -methanamine); 1- ( 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (Yl) amino) methyl) piperidin-1-yl) -2,2-dimethylpropan-1-one (1- (4-((((1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) piperidin-1-yl) -2,2-dimethylpropan-1-one); N- ((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2 -(1-propylpiperidin-4-yl) ethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7 -yl) piperidin-4-yl) methyl) -2- (1-propylpiperidin-4-yl) ethan-1-amine); 4-(((((1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N, 3-trimethylaniline ( 4-((((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N , N, 3-trimethylaniline); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) pyridine Alk-3-yl) -N- (cyclohexylmethyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl ) pyrrolidin-3-yl) -N- (cyclohexylmethyl) methanamine); 4-(((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] Pyridine-7-yl) pyrrolidin-3-yl) methyl) amino) azacycloheptane-1-carboxylic acid tert-butyl ester (tert-Butyl 4-(((1- (2- (5- chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) azepane-1-carboxylate); 4-(((((1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -3 -Methoxy-N, N-dimethylaniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3- yl) methyl) amino) methyl) -3-methoxy-N, N-dimethylaniline); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo) [1,2-a] pyridine-7-yl) azetidin-3-yl) -N- (3-methylbenzyl) methylamine (1- (1- (2- (5-Chloro- 2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (3-methylbenzyl) methanamine); 4-(((((1- (2- (5 (5 -Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidin-3-yl) methyl) amino) methyl) -N, N, 2-trimethylaniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) methyl) -N, N, 2-trimethylaniline); 4-(((((1- (2- (5- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N, 2 -Trimethylaniline (4-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N, 2-trimethylaniline); 4-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) -2-methoxy-N, N-dimethylaniline (4-((((1- (2- ( 5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -2-methoxy-N, N-dimethylaniline); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1 -Isobutylpiperidin-4-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1-isobutylpiperidin-4-yl) methyl) methanamine); 2-((((((1- (2- (5-chloro-2,4-di Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino ) methyl) piperidine-1-carboxylate); 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- ) Azetidin-3-yl) methyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-((((1- (2- (5- chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -piperidine-1-carboxylate); 1- (1- (tert Butyl) pyrrolidin-3-yl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Pyrrolidin-3-yl) methyl) methylamine (1- (1- (tert-Butyl) pyrrolidin-3-yl) -N-((1- (2- (5-chloro-2,4-dimethoxyphenyl ) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) methanamine); 1- (1- (methyl) pyrrolidin-3-yl) -N-((1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) methylamine (1- (1 -(methyl) pyrrolidin-3-yl) -N-((1- (2- (5-chloro-2,4-dimethoxyphe nyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpyrrolidin-3-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpyrrolidin-3-yl) methyl) methanamine ); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin- 4-yl) methyl) -4-methylcyclohexan-1-amine); 6-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2- a) Pyridine-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylpyridin-3-amine (6-((((1- (2- ( 5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -N, N-dimethylpyridin-3-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (2-fluorobenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (2-fluorobenzyl) methanamine); 1- (4- (2-(((1- (2- (5-chloro-2,4-dimethoxyphenyl)) imidazole ([1,2-a] pyridine-7-yl) piperidin-4-yl) methyl) amino) ethyl) piperidin-1-yl) -2,2-dimethylpropan-1-one (1- (4- (2-(((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) ethyl) piperidin-1-yl) -2,2-dimethylpropan-1-one); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [ 1,2-a) pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-cycloheptylethyl-1-amine (N-((1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-cycloheptylethan-1-amine); 1- (1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpiperidin-3-yl) methyl ) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1- methylpiperidin-3-yl) methyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidin-3-yl) -N-((1-ethylpiperidin-3-yl) methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-3-yl) methyl) methanamine); N-((1- (2- (5-chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -4-ethylcyclohex-1-amine (N -((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -4-ethylcyclohexan-1-amine) ; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) -N- (3-fluorobenzyl) methylamine 1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl ) -N- (3-fluorobenzyl) methanamine; 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Piperidin-4-yl) -N- (4-fluoro-3-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluoro-3-methylbenzyl) methanamine); 3-(((((1- (2- (5-chloro-2,4-di Methoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-3-yl) methyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert -Butyl 3-((((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-3-yl) met hyl) amino) methyl) -piperidine-1-carboxylate); 2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) azetidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline (2-(((((1- (2- (5-Chloro -2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) azetidin-3-yl) methyl) amino) methyl) -N, N-dimethylaniline); 1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4-fluoro-3-methylbenzyl ) Methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (4- fluoro-3-methylbenzyl) methanamine); 3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl ) Piperidin-4-yl) methyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-((((1- (2- (5-chloro-2, 4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino) methyl) -piperidine-1-carboxylate); 1- (1- (2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N-((1- (cyclobutylmethyl) -piperidine -4-yl) methyl) -methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] pyridin-7-yl) piperidin-4-yl) -N-((1- (cyclobutylmethyl) -piperidin-4-yl) methyl) -methanamine); 1- (1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2,3-dimethylbenzyl) -methylamine ( 1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2,3-dimethylbenzyl)- methanamine); N- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine-3- (Ethyl) ethyl) -1-ethylpiperidine-4-amine (N- (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7 -yl) pyrrolidin-3-yl) ethyl) -1-ethylpiperidin-4-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a) pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl) ethan-1- amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl)- N- (2-cyclohexylethyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperid in-4-yl) -N- (2-cyclohexylethyl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a) pyridine-7-yl) piperidin-4-yl) -N- (2-fluoro-3-methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2, 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl)-N- (2-fluoro-3-methylbenzyl) methanamine); 1- (1- (2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-methoxy-5-methylbenzyl (Methyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2- methoxy-5-methylbenzyl) methanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidine -3-yl) -N- (2-cyclopentylethyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2-cyclopentylethyl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) ) Imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cycloheptylmethyl) ethyl-1-amine (1- (1- (2- (5- Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (cycloheptylmethyl) ethan-1-amine); 1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-fluoro-5- Methylbenzyl) methylamine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-fluoro-5-methylbenzyl) methanamine); N-((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- (Yl) piperidin-4-yl) methyl) -2- (cyclohex-1-en-1-yl) ethyl-1-amine (N-((1- (2- (5-Chloro-2,4 -dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) -2- (cyclohex-1-en-1-yl) ethan-1-amine); N-(( 1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-ring Amylethyl-1-amine (N-((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) -2-cyclopentylethan-1-amine); 4- (3-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine- 7-yl) pyrrolidin-3-yl) methyl) amino) propyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (3-(((1- (2- (5- ( chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) methyl) amino) propyl) piperidine-1-carboxylate); 4- (2-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) Ethyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (2-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a ] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) ethyl) piperidine-1-carboxylate); N1- (1- (1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) -N4, N4-dimethylcyclohexane-1,4-diamine (N1- ( 1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) -N4, N4-dimethylcyclohexane-1, 4-diamine); 4-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piper Pyridin-4-yl) ethyl) amino) methyl) -benzonitrile (4-(((2- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2- a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -benzonitrile); 4-(((2- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridine-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4 -(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-y l) ethyl) amino) methyl) -piperidine-1-carboxylate); N-benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperidin-4-yl) ethyl-1-amine (N-Benzyl-1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1, 2-a] pyridin-7-yl) piperi din-4-yl) ethan-1-amine); 3-(((1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3 -(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) methyl)- piperidine-1-carboxylate); 4- (3-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7 -Yl) pyrrolidin-3-yl) ethyl) amino) propyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (3-((1- (1- (2- ( 5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) propyl) -piperidine-1-carboxylate); 1- (1- ( 2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpiperidine Pyridin-4-yl) methyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] py ridin-7-yl) pyrrolidin-3-yl) -N-((1-methylpiperidin-4-yl) methyl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4 -Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- (2- (1-propylpiperidin-4-yl) ethyl ) Ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- ( 2- (1-propylpiperidin-4-yl) ethyl) ethan-1-amine); 3-(((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazole (1,2-a) pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -pyrrolidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-(((( 2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -pyrrolidine-1- carboxylate); 4- (3-((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridine-7-yl) Piperidin-4-yl) ethyl) amino) -propyl) piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4- (3-((1- (1- (2- (5-chloro -2,4-dimethoxyphenyl) -imidazo [1,2-a] pyridin-7-yl) piperidin- 4-yl) ethyl) amino) -propyl) piperidine-1-carboxylate); 2-(((((1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) methyl) amino ) Methyl) -4-methylphenol (2-(((((1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4 -yl) methyl) amino) methyl) -4-methylphenol); 4-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2 -a) pyridine-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl ester (tert-Butyl 4-(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylate); 3- ((((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) Ethyl) amino) methyl) -pyrrolidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3-((((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -pyrrolidine-l-carboxylate); 2- (1- (2- (5-chloro-2,4- Dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) ethyl-1-amine (2- (1- ( 2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) ethan-1-amine); 1- (1 -(2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Pyrrolidin-3-yl) -N-((1-isopropylpyrrolidin-3-yl) methyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4- dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-isopropylpyrrolidin-3-yl) methyl) ethan-1-amine); 1- (tert-butyl ) -N- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl ) Ethyl) piperidine-4-amine (1- (tert-Butyl) -N- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a) pyridin -7-yl) pyrrolidin-3-yl) ethyl) piperidin-4-amine); 3-(((((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl)) Imidazo- [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylic acid tert-butyl tert-butyl 3- ( ((2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine -1-carboxylate); N-benzyl-2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7-yl) Piperidin-4-yl) ethyl-1-amine (N-Benzyl-2- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [l, 2-a] pyridin-7-yl) piperidin-4-yl) ethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridine-7- base) Pyridin-4-yl) -N- (cyclopentylmethyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin -7-yl) piperidin-4-yl) -N- (cyclopentylmethyl) ethan-1-amine); 3-(((((1- (1- (2- (5-chloro-2,4-dimethoxy) Phenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) methyl) pyrrolidine-1-carboxylic acid tert-butyl ester (tert-Butyl 3 -(((1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) ethyl) amino) methyl) pyrrolidine-1-carboxylate); N- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidine Pyridin-4-yl) ethyl) cyclohexylamine (N- (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin -4-yl) ethyl) cyclohexanamine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piper Pyridin-4-yl) -N-phenethylethyl-1-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl ) piperidin-4-yl)-N-phenethylethan-1-amine); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] Pyridine-7-yl) piperidin-4-yl) -N- (2-cyclopentylethyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4-d imethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (2-cyclopentylethyl) ethan-1-amine); 3-(((((1- (1- (2 -(5-chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) ethyl) amino) methyl) -piper Tert-Butyl 3-(((1- (1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo- [1,2-a) pyridin-7- yl) piperidin-4-yl) ethyl) amino) methyl) -piperidine-1-carboxylate); 1- (1- (2- (5-chloro-2,4-dimethoxyphenyl) imidazo [1 , 2-a] pyridine-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) ethyl-1-amine (1- (1- (2- (5-Chloro-2,4- dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) piperidin-4-yl) -N- (cyclohexylmethyl) ethan-1-amine); and 1- (1- (2- (5-chloro-2 , 4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N-((1-ethylpiperidin-4-yl) methyl ) Propan-2-amine (1- (1- (2- (5-Chloro-2,4-dimethoxyphenyl) imidazo [1,2-a] pyridin-7-yl) pyrrolidin-3-yl) -N- ( (1-ethylpiperidin-4-yl) methyl) propan-2-amine); and the aforementioned pharmaceutically acceptable salts.     A pharmaceutical composition comprising, as an active ingredient, a compound according to any one of claims 1 to 10 or a pharmaceutically acceptable salt thereof.         The use of the pharmaceutical composition according to item 11 of the application for treating or preventing cancer.         A pharmaceutical composition according to item 12 of the patent application, wherein the cancer is selected from the group consisting of lung cancer, cervical cancer, bladder cancer, esophageal cancer, and osteosarcoma ( osteosarcoma), prostate cancer and soft tissue tumors.         A method for treating or preventing a disease related to the overexpression of SUV39H2, comprising administering to a subject in need an effective amount of a compound described in any one of claims 1 to 10 or a pharmaceutically acceptable compound thereof Accepted salt.         A method according to claim 14 in which the disease is cancer.         A use of a compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 10 of the scope of the patent application, which is a medicament for treating or preventing diseases related to SUV39H2 overexpression.