KR20190096917A - Heterocylic compound as a protein kinase inhibitor - Google Patents

Abstract

The present invention provides a novel compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof having a protein kinase inhibitory activity. The compound, the stereoisomer thereof, or the pharmaceutically acceptable salt thereof according to the present invention exhibits the protein kinase inhibitory activity, thereby being effective in preventing or treating protein kinase related diseases such as cancer, autoimmune diseases, neurological diseases, metabolic diseases or infections.

Description

Heterocylic compound as a protein kinase inhibitor

The present invention relates to novel compounds that can be usefully used in the prevention or treatment of diseases associated with them by inhibiting protein kinase activity and the use thereof.

Protein kinases are enzymes that phosphorylate other proteins to regulate the activity, location and function of proteins to control various intracellular processes. The dysregulation of these protein kinases is closely linked to disease mechanisms such as cancer, autoimmune diseases, neurological diseases, metabolic diseases or infections.

JAK (Janus Kinase) is a protein with a molecular weight of 120-130 KDa consisting of about 1150 amino acids, and is classified into four types: JAK1, JAK2, JAK3, and TYK2. Yanuskinase is located in the intracellular receptors of inflammatory cytokines, and inflammatory cytokines (IL-2, IL-4, IL-6, IL-7, IL-9, IL15, IL-21, GM-CSF, G-CSF , EPO, TPO, IFN-a, IFN-b, IFN-g, etc.) bind to the receptor and deliver inflammatory cytokine signals intracellularly through phosphorylation and interaction with STAT molecules. Excessive activation of signal transduction through these various inflammatory cytokines results in the body's immune system attacking the human body, resulting in autoimmune diseases. Therefore, the development of a drug that inhibits the receptor kinase of inflammatory cytokines in autoimmune diseases is expected to be able to confirm the improved therapeutic effect than conventional therapeutics.

It is an object of the present invention to provide novel compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof which exhibit protein kinase inhibitory activity.

The present invention also aims to provide a method for preparing a compound of the present invention, a stereoisomer thereof or a pharmaceutically acceptable salt thereof.

It is an object of the present invention to provide a pharmaceutical composition for the treatment or prevention of protein kinase related diseases containing a compound of the present invention, a stereoisomer thereof or a pharmaceutically acceptable salt thereof as an active ingredient.

The invention also aims to provide a method for the treatment or prevention of a protein kinase related disease comprising administering a therapeutically effective amount of a compound of the invention, a stereoisomer thereof or a pharmaceutically acceptable salt thereof.

The present invention also aims to provide the use of a compound of the present invention, a stereoisomer thereof or a pharmaceutically acceptable salt thereof for the manufacture of a medicament for the prophylaxis or treatment of a protein kinase related disease.

protein Kinase  Inhibitor compound

In order to solve the above problems, the present invention provides a compound of Formula 1, a stereoisomer thereof or a pharmaceutically acceptable salt thereof.

[Formula 1]

Where

X is CA ₃ or N,

Y is CA ₄ or N,

Z is N or N-O,

A ₁ to A ₄ are each independently H or C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, C (═O) —OH, C (═O) —O—C 1 -C 6 alkyl, S (═O) ₂ -C 1 -C 6 alkyl, aryl or heteroaryl,

B ₁ is-(CH ₂ ) _m- , -C (= O)-, -C (= S)-, -C (= NR ₁ )-, -C (= O) -NR _1- , -S ( = O) ₂ -or nothing (null) {where one or more H of-(CH ₂ ) _m -can be substituted with C1-C6 alkyl, halogen or cyano, or linked together with one or more carbon atoms Can form a ring},

B ₂ is H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, 5-6 membered heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl-aryl or C 1 -C 6 alkyl-heteroaryl, wherein C 3 -C 7 One or more H of cycloalkyl, 5-6 membered heterocycloalkyl, aryl, heteroaryl, C1-C6 alkyl-aryl or C1-C6 alkyl-heteroaryl may be substituted with C1-C6 alkyl, hydroxy or halogen} ,

B ₃ is H or C 1 -C 6 alkyl,

Cyclic linker is C3-C7 cycloalkyl, C3-C7 cycloalkenyl, 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl

C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 hydroxyalkyl, C 1 -C 6 cyanoalkyl, C 1 -C 6 haloalkyl, hydroxy, cyano, halogen, C (═O) —OH, C (═O) —O—C 1 -C 6 alkyl, S (═O) ₂ -C 1 -C 6 alkyl, aryl or heteroaryl,

Or C ₁ and C ₂ may be linked to each other through one or more carbon atoms to form a bicyclic ring or a spy ring,

,

또는 아무 것도 아니고 (null) {여기서, -(CH₂)_m- 또는 -(CH₂)_m-NR₁- 의 하나 이상의 H는 C1-C6알킬, 할로겐 또는 시아노로 치환될 수 있고, 또는 하나 이상의 탄소 원자와 함께 서로 연결되어 고리를 형성할 수 있고,

또는

의 하나 이상의 H는 C1-C6알킬, C1-C6히드록시알킬, C1-C6할로알킬 또는 C1-C6시아노알킬로 치환될 수 있음}, D ₁ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

,

Or not blank (null) {wherein, - (CH _{2) m} - or _{- (CH 2) m -NR 1} - one or more H, C1-C6 alkyl, halogen or cyano and may be substituted, or one or more of Can be linked together with carbon atoms to form a ring,

or

At least one H may be substituted with C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl or C 1 -C 6 cyanoalkyl,

D ₂ is -C (= O)-, -C (= O) -CH ₂ -C (= O)-, -C (= S)-, -S (= O) ₂ -or nothing (null ) {Where one or more H of —C (═O) —CH ₂ —C (═O) — may be substituted with C 1 -C 6 alkyl or halogen},

또는 아무 것도 아니고 (null) {여기서, -(CH₂)_m- 또는 -(CH₂)_m-NR₁- 의 하나 이상의 H는 C1-C6알킬, 할로겐 또는 시아노로 치환될 수 있고, 또는 하나 이상의 탄소 원자와 함께 서로 연결되어 고리를 형성할 수 있음},D ₃ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

Or not blank (null) {wherein, - (CH _{2) m} - or _{- (CH 2) m -NR 1} - one or more H, C1-C6 alkyl, halogen or cyano and may be substituted, or one or more of Together with carbon atoms to form a ring},

, 아릴 또는 헤테로아릴이고D ₄ is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, S (= 0) ₂ -C ₁ -C6 alkyl, C3-C7 cycloalkyl,

, Aryl or heteroaryl

Wherein one or more H of C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl or C 1 -C 6 cyanoalkyl is C 3 -C 7 cycloalkyl Can be substituted,

의 하나 이상의 H는 C1-C6알킬, C1-C6할로알킬, C1-C6시아노알킬, 시아노, 할로겐, -C(=O)-R₄ 또는 -C(=O)-O-R₄ 로 치환될 수 있고, C3-C7cycloalkyl or

At least one H may be substituted with C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, cyano, halogen, —C (═O) —R ₄ or —C (═O) —OR ₄ Can,

, 아릴 또는 헤테로아릴로 치환될 수 있음 [이때,

의 하나 이상의 H는 C1-C6알킬 또는 (=O) 로 치환될 수 있음]}, One or more H of aryl or heteroaryl is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 cyanoalkyl, C 1 -C 6 thioalkyl, hydroxy, cyano , Nitro, halogen, -C (= 0) -R ₄ , -C (= 0) -NR ₁ -R ₄ , -S (= 0) ₂ -R ₄ , -S (= 0) ₂ -NR _1- R ₄ , -NR ₁ -R _5,

, May be substituted with aryl or heteroaryl [wherein

At least one H may be substituted with C 1 -C 6 alkyl or (═O)]},

R ₁ and R ₂ are each independently H or C 1 -C 6 alkyl,

R ₃ is H, C 1 -C 6 alkyl, —C (═O) —R ₄ , —C (═O) —OR ₄ , —S (═O) ₂ —R ₄ or —S (═O) ₂ -NR ₁ -R ₄ and {where W is -O-, -C (= O)-or -S (= O) ₂ -then R ₃ is nothing (null)},

R ₄ is H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,

, 아릴 또는 헤테로아릴이고 {여기서,

의 하나 이상의 H는 C1-C6알킬 또는 (=O) 로 치환될 수 있고, 아릴 또는 헤테로아릴의 하나 이상의 H는 C1-C6알킬 또는 할로겐으로 치환될 수 있음},R ₅ is H, C 1 -C 6 alkyl,

, Aryl or heteroaryl, wherein

At least one H may be substituted with C 1 -C 6 alkyl or (═O) and at least one H of aryl or heteroaryl may be substituted with C 1 -C 6 alkyl or halogen.

V is -CH- or -N-,

W is -CH-, -N-, -O-, -S-, -C (= 0)-, -S (= 0)-or -S (= 0) ₂ -where V is -CH If-W is not -CH-},

a to d are each independently 1, 2 or 3,

m is 1, 2 or 3.

According to one embodiment of the invention,

X is CA ₃ or N,

Y is CA ₄ or N,

Z is N or N-O,

A ₁ to A ₄ are each independently H or C 1 -C 6 alkyl or C 1 -C 6 cyanoalkyl,

B ₁ is-(CH ₂ ) _m- , -C (= O)-, -C (= S)-, -C (= NR ₁ )-, -C (= O) -NR _1- , -S ( = O) ₂ -or nothing (null) {where one or more H of-(CH ₂ ) _m -can be substituted with C1-C6 alkyl, halogen or cyano, or linked together with one or more carbon atoms Can form a ring},

B ₂ is H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, aryl, heteroaryl or C 1 -C 6 alkyl-aryl, wherein one of C 3 -C 7 cycloalkyl, aryl, heteroaryl or C 1 -C 6 alkyl-aryl Or more H may be substituted with C1-C6 alkyl},

B ₃ is H or C 1 -C 6 alkyl,

Cyclic linker is C3-C7 cycloalkyl, C3-C7 cycloalkenyl, 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl,

C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl, C 1 -C 6 haloalkyl, hydroxy, cyano, halogen, C (═O) —OH, C (═O) —O—C 1 -C 6 alkyl , Or aryl,

Or C ₁ and C ₂ may be linked to each other through one or more carbon atoms to form a bicyclic ring or a spy ring,

,

또는 아무 것도 아니고 (null) {여기서, -(CH₂)_m- 또는 -(CH₂)_m-NR₁- 의 하나 이상의 H는 C1-C6알킬 또는 할로겐으로 치환될 수 있고, 또는 하나 이상의 탄소 원자와 함께 서로 연결되어 고리를 형성할 수 있고,

,

또는

의 하나 이상의 H는 C1-C6알킬 또는 C1-C6시아노알킬로 치환될 수 있음}, D ₁ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

,

Or none (null) {where one or more H of — (CH ₂ ) _m — or — (CH ₂ ) _m —NR ₁ — may be substituted with C 1 -C 6 alkyl or halogen, or one or more carbon atoms Together with each other to form a ring,

,

or

At least one H may be substituted with C 1 -C 6 alkyl or C 1 -C 6 cyanoalkyl},

D ₂ is -C (= O)-, -C (= O) -CH ₂ -C (= O)-, -C (= S)-, -S (= O) ₂ -or nothing (null ) Wherein one or more H of —C (═O) —CH ₂ —C (═O) — may be substituted with C 1 -C 6 alkyl},

또는 아무 것도 아니고 (null) {여기서, -(CH₂)_m- 또는 -(CH₂)_m-NR₁- 의 하나 이상의 H는 시아노로 치환될 수 있음},D ₃ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

Or not blank (null) {wherein, - (CH _{2) m} - or _{- (CH 2) m -NR 1} - that one or more of H is cyano may be substituted},

, 아릴 또는 헤테로아릴이고D ₄ is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, S (= 0) ₂ -C ₁ -C6 alkyl, C3-C7 cycloalkyl,

, Aryl or heteroaryl

Wherein one or more H of C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl or C 1 -C 6 cyanoalkyl is C 3 -C 7 cycloalkyl Can be substituted,

의 하나 이상의 H는 C1-C6알킬, C1-C6할로알킬, C1-C6시아노알킬, 시아노, 할로겐 또는 -C(=O)-O-R₄ 로 치환될 수 있고, C3-C7cycloalkyl or

At least one H may be substituted with C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, cyano, halogen or —C (═O) —OR ₄ ,

로 치환될 수 있음 [이때,

의 하나 이상의 H는 (=O) 로 치환될 수 있음]}, One or more H of aryl or heteroaryl is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 thioalkyl, hydroxy, cyano, nitro, halogen, -C (= 0) -R ₄ , -C (= 0) -NR ₁ -R ₄ , -S (= 0) ₂ -R ₄ , -S (= 0) ₂ -NR ₁ -R ₄ , -NR ₁ -R ₅ or

Can be substituted with [In this case,

At least one H may be substituted with (= O)]},

R ₁ and R ₂ are each independently H or C 1 -C 6 alkyl,

R ₃ is H, C 1 -C 6 alkyl, —C (═O) —R ₄ , —C (═O) —OR ₄ , —S (═O) ₂ —R ₄ or —S (═O) ₂ -NR ₁ -R ₄ and {where W is -O-, -C (= O)-or -S (= O) ₂ -then R ₃ is nothing (null)},

R ₄ is H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,

또는 아릴이고 {여기서,

의 하나 이상의 H는 (=O) 로 치환될 수 있고, 아릴 또는 헤테로아릴의 하나 이상의 H는 C1-C6알킬 또는 할로겐으로 치환될 수 있음},R ₅ is H,

Or aryl, where {

At least one H may be substituted with (═O) and at least one H of aryl or heteroaryl may be substituted with C 1 -C 6 alkyl or halogen},

V is -CH- or -N-,

W is -CH-, -N-, -O-, -S-, -C (= 0)-, -S (= 0)-or -S (= 0) ₂ -where V is -CH If-W is not -CH-},

a to d are each independently 1, 2 or 3,

m can be 1 or 2.

According to another embodiment of the present invention,

X is CA ₃ ,

Y is CA ₄ ,

Z is N or N-O,

A ₁ to A ₄ are each independently H or C 1 -C 6 alkyl or C 1 -C 6 cyanoalkyl,

B ₁ is-(CH ₂ ) _m- , -C (= O)-, -C (= S)-, -C (= NR ₁ )-, -C (= O) -NR _1- , -S ( = O) ₂ -or nothing (null),

B ₂ is H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, aryl, heteroaryl or C 1 -C 6 alkyl-aryl, wherein one of C 3 -C 7 cycloalkyl, aryl, heteroaryl or C 1 -C 6 alkyl-aryl Or more H may be substituted with C1-C6 alkyl},

B ₃ is H,

Cyclic linker is C3-C7 cycloalkyl, C3-C7 cycloalkenyl, 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl,

C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl, C 1 -C 6 haloalkyl, hydroxy, cyano, halogen, C (═O) —OH, C (═O) —O—C 1 -C 6 alkyl , Or aryl,

Or C ₁ and C ₂ may be linked to each other through one or more carbon atoms to form a bicyclic ring or a spy ring,

,

또는 아무 것도 아니고 (null) {여기서, -(CH₂)_m- 또는 -(CH₂)_m-NR₁- 의 하나 이상의 H는 C1-C6알킬 또는 할로겐으로 치환될 수 있고, 또는 하나 이상의 탄소 원자와 함께 서로 연결되어 고리를 형성할 수 있고,

,

또는

의 하나 이상의 H는 C1-C6알킬 또는 C1-C6시아노알킬로 치환될 수 있음}, D ₁ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

,

Or none (null) {where one or more H of — (CH ₂ ) _m — or — (CH ₂ ) _m —NR ₁ — may be substituted with C 1 -C 6 alkyl or halogen, or one or more carbon atoms Together with each other to form a ring,

,

or

At least one H may be substituted with C 1 -C 6 alkyl or C 1 -C 6 cyanoalkyl},

D ₂ is -C (= O)-, -C (= O) -CH ₂ -C (= O)-, -C (= S)-, -S (= O) ₂ -or nothing (null ) Wherein one or more H of —C (═O) —CH ₂ —C (═O) — may be substituted with C 1 -C 6 alkyl},

또는 아무 것도 아니고 (null) {여기서, -(CH₂)_m- 또는 -(CH₂)_m-NR₁- 의 하나 이상의 H는 시아노로 치환될 수 있음},D ₃ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

Or not blank (null) {wherein, - (CH _{2) m} - or _{- (CH 2) m -NR 1} - that one or more of H is cyano may be substituted},

, 아릴 또는 헤테로아릴이고D ₄ is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, S (═O) ₂ -C 1 -C 6 alkyl, C 3 -C 7 Cycloalkyl,

, Aryl or heteroaryl

Wherein one or more H of C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 haloalkyl or C 1 -C 6 cyanoalkyl may be substituted with C 3 -C 7 cycloalkyl,

의 하나 이상의 H는 C1-C6알킬, C1-C6할로알킬, C1-C6시아노알킬, 시아노, 할로겐 또는 -C(=O)-O-R₄ 로 치환될 수 있고, C3-C7cycloalkyl or

At least one H may be substituted with C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, cyano, halogen or —C (═O) —OR ₄ ,

로 치환될 수 있음 [이때,

의 하나 이상의 H는 (=O) 로 치환될 수 있음]}, One or more H of aryl or heteroaryl is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 thioalkyl, hydroxy, cyano, nitro, halogen, -C (= 0) -R ₄ , -C (= 0) -NR ₁ -R ₄ , -S (= 0) ₂ -R ₄ , -S (= 0) ₂ -NR ₁ -R ₄ , -NR ₁ -R ₅ or

Can be substituted with [In this case,

At least one H may be substituted with (= O)]},

R ₁ and R ₂ are each independently H or C 1 -C 6 alkyl,

R ₃ is H, C 1 -C 6 alkyl, —C (═O) —R ₄ , —C (═O) —OR ₄ , —S (═O) ₂ —R ₄ or —S (═O) ₂ -NR ₁ -R ₄ and {where W is -O-, -C (= O)-or -S (= O) ₂ -then R ₃ is nothing (null)},

R ₄ is H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,

또는 아릴이고 {여기서,

의 하나 이상의 H는 (=O) 로 치환될 수 있고, 아릴 또는 헤테로아릴의 하나 이상의 H는 C1-C6알킬 또는 할로겐으로 치환될 수 있음},R ₅ is H,

Or aryl, where {

At least one H may be substituted with (═O) and at least one H of aryl or heteroaryl may be substituted with C 1 -C 6 alkyl or halogen},

V is -CH- or -N-,

W is -CH-, -N-, -O-, -S-, -C (= 0)-, -S (= 0)-or -S (= 0) ₂ -where V is -CH If-W is not -CH-},

a to d are each independently 1, 2 or 3,

m can be 1 or 2.

According to another embodiment of the present invention,

X is CA ₃ ,

Y is N,

Z is N,

A ₁ to A ₃ are each independently H or C 1 -C 6 alkyl,

B ₁ is -C (= 0)-

B ₂ is C 3 -C 7 cycloalkyl or aryl, wherein one or more H of C 3 -C 7 cycloalkyl or aryl may be substituted with C 1 -C 6 alkyl;

B ₃ is H or C 1 -C 6 alkyl,

Cyclic linker is 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl,

C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl or halogen,

Or C ₁ and C ₂ may be linked to each other through one or more carbon atoms to form a bicyclic ring,

D ₁ is-(CH ₂ ) _m- , -NR ₁ -or nothing (null),

D ₂ is -C (= O)-, -C (= S)-, -S (= O) ₂ -or nothing (null),

D ₃ is-(CH ₂ ) _m- , -NR _1- , -O- or nothing (null),

, 아릴 또는 헤테로아릴이고D ₄ is C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, C 3 -C 7 cycloalkyl,

, Aryl or heteroaryl

의 하나 이상의 H는 C1-C6알킬 또는 시아노 로 치환될 수 있고, {Wherein C3-C7cycloalkyl or

At least one H may be substituted with C 1 -C 6 alkyl or cyano,

One or more H of aryl or heteroaryl may be substituted by C ₁ -C 6 alkyl, cyano, halogen or —C (═O) —NR ₁ —R ₄ },

R ₁ is H or C ₁ -C 6 alkyl,

R ₄ is H,

V is -CH- or -N-,

W is -O- or -S (= 0) _2- ,

a and b are each independently 1, 2 or 3,

m can be 1 or 2.

According to another embodiment of the present invention,

X is N,

Y is CA ₄ ,

Z is N,

A ₁ , A ₂ and A ₄ are each independently H or C 1 -C 6 alkyl,

B ₁ is -C (= 0)-

B ₂ is C 3 -C 7 cycloalkyl, wherein one or more H of C 3 -C 7 cycloalkyl can be substituted with C 1 -C 6 alkyl,

B ₃ is H,

Cyclic linker is aryl

C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl or halogen,

D ₁ is-(CH ₂ ) _m -or -NR _1- ,

D ₂ is -S (= O) ₂ -or nothing (null),

D ₃ is nothing (null),

D ₄ is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or heteroaryl

Wherein one or more H of C 1 -C 6 alkyl or C 1 -C 6 haloalkyl may be substituted with C 3 -C 7 cycloalkyl,

At least one H of heteroaryl may be substituted with C 1 -C 6 alkyl},

R ₁ is H,

m can be 1 or 2.

According to another embodiment of the present invention,

X is N,

Y is N,

Z is N,

A ₁ and A ₂ are each independently H or C 1 -C 6 alkyl,

B ₁ is -C (= 0)-

B ₂ is C 3 -C 7 cycloalkyl, wherein one or more H of C 3 -C 7 cycloalkyl can be substituted with C 1 -C 6 alkyl,

B ₃ is H,

Cyclic linker is aryl

C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl or halogen,

D ₁ is-(CH ₂ ) _m , -NR _1- , -NR ₁ -or -O-,

D ₂ is -S (= O) ₂ -or nothing (null),

D ₃ is nothing (null),

, 아릴 또는 헤테로아릴이고D ₄ is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl,

, Aryl or heteroaryl

Wherein one or more H of C 1 -C 6 alkyl or C 1 -C 6 haloalkyl may be substituted with C 3 -C 7 cycloalkyl,

One or more H of aryl or heteroaryl may be substituted with cyano or halogen},

R ₁ is H,

V is -N-,

W is -O- or -S (= O) _2- ,

a and b are each independently 1, 2 or 3,

m can be 1 or 2.

In defining the compound of formula (1) throughout this specification, the concepts defined as follows are used. The following definitions also apply to terms that are used individually or as part of a larger group throughout this specification, unless specifically indicated otherwise.

The term "alkyl", when used alone or in combination with "heteroalkyl", refers to a straight, branched or cyclic hydrocarbon radical, each carbon atom being one or more cyano, hydroxy, alkoxy, oxo, And optionally substituted with halogen, carbonyl, sulfonyl, cyanyl and the like.

The term “alkoxy” refers to —O-alkyl, wherein alkyl is as defined above.

The term “heteroalkyl” means an alkyl comprising at least one hetero atom selected from N, O, S.

The term “aryl” means an aromatic group including phenyl, naphthyl, and the like, which may be optionally substituted with one or more alkyl, alkoxy, halogen, hydroxy, carbonyl, sulfonyl, cyanyl, and the like.

The term “hetero cycle” refers to a form that is saturated or partially saturated or aromatic, comprising 1 to 4 heteroatoms selected from N, O, S, and optionally optionally fused with benzo or cycloalkyl.

The term “halo (gen)” means a substituent selected from fluuro, chloro, bromo and iodo.

In addition, the terms and abbreviations used herein have their original meanings unless defined otherwise.

In the present invention, representative examples of the compound represented by Formula 1 are as follows.

Hereinafter, unless otherwise indicated for convenience, the compound of Formula 1 includes all compounds of Formula 1, stereoisomers thereof, or pharmaceutically acceptable salts thereof of the present invention.

The compounds according to the invention may form pharmaceutically acceptable salts. Such pharmaceutically acceptable salts include acids that form non-toxic acid addition salts, for example inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, hydroiodic acid, and the like, tartaric acid, formic acid, citric acid, acetic acid, trichloroacetic acid, tri Acid addition salts formed by organic carbon acids such as fluoroacetic acid, gluconic acid, benzoic acid, lactic acid, fumaric acid, maleic acid, etc., sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid or naphthalenesulfonic acid, and the like. The compound of formula 1 according to the present invention can be converted to its salts by conventional methods.

On the other hand, the compounds according to the invention may have asymmetric carbons and may exist as R or S isomers, racemics, diastereomeric mixtures and individual diastereomers, all of these isomers and mixtures being included within the scope of the invention. That is, when asymmetric carbon (s) is included in the structure of Formula 1, it is to be understood that all stereoisomers are included unless the directions are stated otherwise.

Method for preparing compound of formula 1

The present invention also provides a method of preparing a compound of formula (I). Hereinafter, a method of preparing a compound of Chemical Formula 1 will be described based on exemplary reaction schemes for better understanding of the present invention. However, those skilled in the art to which the present invention pertains may employ various methods based on the structure of Chemical Formula 1 Compounds of Formula 1 may be prepared, all of which should be construed as being within the scope of the present invention. That is, it is to be understood that the preparation of the compound of Formula 1 is possible by arbitrarily combining various synthesis methods described herein or disclosed in the prior art, which are within the scope of the present invention. In the following schemes, all substituents are as defined above, unless otherwise indicated.

Acids, bases, and reaction solvents used in the compounds of the invention can be used without limitation, those generally used in the art. Examples of the acid include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid and hydroiodic acid, and tartaric acid, formic acid, citric acid, acetic acid, adipic acid, trichloroacetic acid, trifluoroacetic acid, gluconic acid, benzoic acid and lactic acid. acid, fumaric acid, it is possible to use the sulfonic acids such as organic carboxylic acid, methanesulfonic acid, benzenesulfonic acid, p- toluenesulfonic acid or naphthalenesulfonic acid, such as maleic acid or the like, has a base NaH, K ₂ CO _3, Na ₂ CO ₃ , NaHCO ₃ , K ₃ PO ₄ , KOH, NaOH, LiOH, n-BuLi, sec-BuLi, LiHMDS can be used, and the reaction solvent is DCM, THF, Dioxane, MeOH, EtOH, Hexane, EtOAC, Ether , DMF, DMSO, toluene, xylene or the like or a mixed solvent thereof may be used.

Synthesis method of the compound of Formula 1 according to the present invention can be illustrated by the following Scheme 1 or Scheme 2.

[Scheme 1]

In Scheme 1

A2, B1, B2, C1, C2, X, Y, Z, cyclic linker is as defined in formula (1),

D and D 'are analogs for introducing D1-D2-D3-D4 or D1-D2-D3-D4 themselves as defined in formula (1).

은 halo = OTf인 경우 하기 반응식 1-1의 방법을 통하여 합성될수 있다. Intermediate compound in Scheme 1

Can be synthesized through the method of Scheme 1-1 when halo = OTf.

Scheme 1-1

In Reaction Scheme 1-1

C1, C2, D 'is the same as in Scheme 1,

() n represents a polygonal ring compound.

In addition to the method of Scheme 1, it may be synthesized through the following Scheme 2.

Scheme 2

In Scheme 2

Compound (III) corresponds to compound (III) of Scheme 1.

A2, B1, B2, C1, C2, X, Y, Z are as defined in formula (1),

D and D 'are analogs for introducing D1-D2-D3-D4 or D1-D2-D3-D4 themselves as defined in formula (1).

Compound (I) in Scheme 1 may be commercially available or synthesized.

The compound of formula 1 of the present invention can be separated or purified by various methods such as crystallization, silica gel column chromatography, etc. from the product of Schemes 1 and 2. As such, the compounds of the present invention, disclosures for their preparation, intermediates and the like can be synthesized by a variety of methods, which are to be construed as being within the scope of the present invention with respect to the preparation of compounds of formula 1 do.

Compositions comprising a compound of formula I, uses thereof, methods of treatment using the same

The present invention provides a pharmaceutical composition for the treatment or prophylaxis of a protein kinase related disease comprising a compound represented by the following formula (I), a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient.

[Formula I]

Formula 1 is as defined above.

Formula 1 compound of the present invention exhibits a protein kinase inhibitory activity, showing a significant effect on the prevention or treatment of protein kinase-related diseases.

In the present invention, the protein kinase-related disease includes cancer, autoimmune disease, neurological disease, metabolic disease or infection.

The compound represented by the formula (1) of the present invention, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof has a protein kinase inhibitory activity, which is remarkably excellent in preventing or treating a protein kinase related disease.

Hereinafter, preferred examples are provided to aid in understanding the present invention. However, the following examples are merely provided to more easily understand the present invention, and the present invention is not limited by the examples.

Various synthesis methods of starting materials for synthesizing the compounds of the present invention are known, and if the starting materials are commercially available, they can be purchased and used from a supplier. Reagent supply sources include, but are not limited to, companies such as Sigma-Aldrich, TCI, Wako, Kanto, Fluorchem, Acros, Alfa, Fluka, Combi-Blocks, Dae-Jung, and the like. In addition, all commercially available materials were used without further purification except as otherwise defined.

Hereinafter, the following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

Production Example N- (4- (4,4,5,5- Tetramethyl -1,3,2- Dioxaboran -2-yl) -1-tosyl-1H- blood Synthesis of Lolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide

[Step 1] Synthesis of 4-chloro-1H-pyrrolo [2,3-b] pyridine 7-oxide 3-chlorobenzoate

4-chloro-7-azaindole (15.0 g, 98.3 mmol) was dissolved in n-butyl acetate / n-heptane = 3/5 (v / v), 800 ml, and 0 at ^o C was added dropwise a m- chloroperoxybenzoic acid (77%, 24.2g, 108.1mmol) slowly, and the mixture was stirred at room temperature for 12 hours. The resulting solid was filtered and dried under reduced pressure to give the title compound (30 g, 94%).

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 13.37 (br s, 1H), 12.90 (br s, 1H), 8.15 (d, J = 6.6 Hz, 1H), 7.89 (m, 2H) 7.68 (d , J = 8.0 Hz, 1H), 7.56 (d, J = 3.1 Hz, 1H), 7.52 (t, J = 8.1 Hz, 1H), 7.20 (d, J = 6.6 Hz, 1H), 6.58 (d, J = 3.1 Hz, 1H).

MS (ESI +) m / z 169, 171 (M + H) ⁺

[Step 2] Synthesis of 4-chloro-1H-pyrrolo [2,3-b] pyridin-6-amine

The compound (30 g, 92.3 mmol) obtained in step 1 was suspended in acetonitrile (300 ml), and dimethyl sulphate (9.6 ml, 101.5 mmol) was added dropwise at room temperature, followed by 55 by heating to ^o C and stirred for 12 hours.

0 reaction mixture ^o Cool to C and add excess ammonia ethanol solution. It warmed to ^o C and stirred for 3 days. After cooling to room temperature, the insoluble solid was filtered off, and the filtrate was concentrated under reduced pressure, dissolved in dichloromethane (1L), washed with 10% aqueous sodium carbonate solution, dried over anhydrous magnesium sulfate, and the filtrate was filtered under reduced pressure. Isolation by column chromatography gave the title compound (10 g, 42.4 mmol).

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.16 (s, 1H), 7.00 (s, 1H), 6.33 (s, 1H), 6.19 (s, 1H), 5.83 (s, 2H)

MS (ESI +) m / z 168, 170 (M + H) ⁺

[Step 3] Synthesis of N- (4-chloro-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide

The compound obtained in step 2 (11.0 g, 65.6 mmol) was dissolved in pyridine (100 ml) and cyclopropanecarbonyl chloride (7.5 g, 72.2 mmol) was 0. ^o was slowly added dropwise at C and stirred at the same temperature for 1 hour. The reaction mixture was added to water (350 ml) and the resulting solid was filtered and dried under reduced pressure to give the title compound (12.7 g, 53.9 mmol).

¹ H NMR (400 MHz, DMSO-d ⁶ ) δ 11.77 (s, 1H), 10.79 (s, 1H), 8.02 (s, 1H), 7.44 (d, 1H), 6.25 (d, 1H), 2.00 ( m, 1H), 0.88 (m, 4H)

MS (ESI +) m / z 236, 238 (M + H) ⁺

[Step 4] Synthesis of N- (4-chloro-1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane carboxamide

The compound obtained in step 3 (12.7 g, 53.9 mmol) was dissolved in dimethylformamide (100 ml) and sodium hydride (3.2 g, 80.8 mmol) was 0. ^o After slowly added dropwise at C, tosyl chloride (11.3 g, 59.3 mmol) was slowly added dropwise and stirred for 30 minutes. Ethyl acetate (300 ml) was added thereto, washed with water (300 ml, twice), dried over anhydrous magnesium sulfate, and the filtrate was filtered under reduced pressure. Separation by column chromatography gave the title compound (13.0 g, 33.3 mmol).

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.13 (s, 1H), 8.16 (m, 3H), 7.80 (s, 1H), 7.42 (m, 2H), 6.74 (s, 1H), 2.34 ( s, 3H), 2.08 (m, 1H), 0.87 (m, 4H)

MS (ESI +) m / z 390, 392 (M + H) ⁺

[Step 5] N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) -1-tosyl-1H-pyrrolo [2,3-b ] Synthesis of pyridin-6-yl) cyclopropanecarboxamide

Compound obtained in step 4 (20.0 g, 51.3 mmol), dipinacolborane (26.0 g, 102.6 mmol), palladium acetate (0.2 g, 1.02 mmol), 2- (dicyclohexyl) phosphinebiphenyl (0.7 g, 2.05 mmol), potassium acetate (10.1 g, 102.6 mmol) was added to dioxane (200 ml) and 100 ^o warmed at C for 2 h. After cooling to room temperature and distillation under reduced pressure, dichloromethane (300 ml) was added and washed with distilled water (300 ml, twice). The separated organic layer was dried over anhydrous magnesium sulfate, and the filtrate was filtered under reduced pressure. Separation by column chromatography gave the title compound (24.0 g, 49.8 mmol).

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.75 (s, 1H), 8.34 (s, 1H), 8.16 (d, 2H), 7.74 (d, 1H), 7.41 (d, 2H), 6.82 ( d, 1H), 2.33 (s, 3H), 2.15 (m, 1H), 1.30 (s, 12H), 0.87 (m, 4H)

Example  1: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) -3- fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

[Step 1]

N- (4-chloro-1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4-chloro-1-tosyl) prepared from Scheme 3 above 4.0 g (10.3 mmol) of -1H-pyrrolo [2,3-b] pyridine-6-yl) cyclopropanecarboxamide) are dissolved in a solution of DMF / H ₂ O = 2: 1 and 2-fluoro-4- (4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline 2.7 g (12.4 mmol), Pd (dppf) Cl ₂ 1.3 g (1.5 mmol), K ₃ PO ₄ 2.6 g (12.4 mmol) was added and the mixture was stirred at 80 ^° C to 90 ^° C for 1 hour. When the reaction was completed, the mixture was cooled to room temperature, water was added, and extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was separated on silica gel column chromatography (n-hexane / ethyl acetate = 2: 1) to give the product N- (4- (4-amino-3-fluorophenyl) -1-tosyl-1H-pyrrolo [2 , 3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-amino-3-fluorophenyl) -1-tosyl-1H-pyrrolo [2,3-b] pyridine-6- yl) cyclopropanecarboxamide) was obtained.

MS (ESI +) m / z 465 (M + H) ⁺

[Step 2]

N- (4- (4-amino-3-fluorophenyl) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (100 obtained in step 1 above) mg) was added to dichloromethane and Et ₃ N, 3 equiv. 2 equivalents of ethanesulfonyl chloride was added to the mixture, followed by stirring at room temperature. After the reaction was completed, the mixture was added with d-HCl, extracted with dichloromethane, and the organic layer was separated. The mixture was concentrated and then dissolved in a MeOH / THF (1: 1) solution, 2N aqueous sodium hydroxide solution was added and stirred at 30-40 ^° C. for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and saturated NH ₄ Cl aqueous solution was added with stirring. The resulting solid was filtered to give N- (4- (4- (ethylsulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide Obtained.

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.66 (s, 1H), 9.82 (s, 1H), 8.02 (s, 1H), 7.64-7.52 (m, 3H), 7.49-7.41 (m, 1H), 6.61-6.53 (m, 1H), 3.18 (q, J = 7.2 Hz, 2H), 2.04 (dd, J = 5.0, 10.1 Hz, 1H), 1.29 (t, J = 7.3 Hz, 3H), 0.89-0.78 (m, 4H).

MS (ESI +) m / z 403 (M + H) ⁺

Examples 2 to 213

In Examples 2 to 213, the synthesis was carried out in the same manner as in Example 1, or prepared using a suitable reactant in consideration of the structure of Scheme 1 and the compound to be prepared.

Example  2: N- (4- (4-((3,4- Difluorophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((3,4-difluorophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

MS (ESI +) m / z 469 (M + H) ⁺

Example  3: N- (4- (4-((3- Fluoropropyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((3-fluoropropyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 7.89 (s, 1H), 7.82-7.74 (m, 2H), 7.48-7.37 (m, 2H), 7.32 (d, J = 3.6 Hz, 1H), 6.60 (d, J = 3.6 Hz, 1H), 4.59 (s, 1H), 4.47 (s, 1H), 3.27 (d, J = 5.6 Hz, 1H), 2.32-2.10 (m, 2H), 1.12 (d , J = 6.1 Hz, 1H), 0.95 (ddt, J = 3.1, 8.1, 40.7 Hz, 5H).

MS (ESI +) m / z 417 (M + H) ⁺

Example  4: N- (4- (4- ( Ethylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  (N- (4- (4- ( ethylsulfonamido ) phenyl ) -1H- pyrrolo [2,3- b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.59 (s, 1H), 10.01 (s, 1H), 7.99 (s, 1H), 7.75-7.63 (m, 2H), 7.46-7.29 (m, 3H), 6.54 (dd, J = 1.9, 3.5 Hz, 1H), 3.17 (d, J = 7.4 Hz, 2H), 2.06 (d, J = 16.6 Hz, 1H), 1.23 (t , J = 7.3 Hz, 4H), 0.89-0.75 (m, 4H).

MS (ESI +) m / z 385 (M + H) ⁺

Example  5: N- (4- (4- ( Propylsulfonylamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( propylsulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 10.00 (s, 1H), 8.00 (s, 1H), 7.81-7.64 (m, 2H), 7.38 (ddd, J = 2.4, 6.2, 8.6 Hz, 3H), 6.54 (dd, J = 1.9, 3.5 Hz, 1H), 3.22-3.05 (m, 2H), 2.06 (d, J = 16.5 Hz, 1H) , 1.72 (td, J = 6.2, 8.3, 8.8 Hz, 2H), 0.96 (t, J = 7.4 Hz, 4H), 0.81 (ddd, J = 2.6, 6.4, 10.6 Hz, 5H).

MS (ESI +) m / z 399 (M + H) ⁺

Example  6: N- (4- (4- ( Butyl sulfon amido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  (N- (4- (4- ( butylsulfonamido ) phenyl ) -1H- pyrrolo [2,3- b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.59 (s, 1H), 10.13-9.90 (m, 1H), 7.99 (s, 1H), 7.72-7.64 (m, 2H ), 7.42-7.30 (m, 3H), 6.54 (dd, J = 1.8, 3.5 Hz, 1H), 3.21-3.10 (m, 2H), 2.09-1.99 (m, 1H), 1.73-1.61 (m, 2H ), 1.38 (dt, J = 7.5, 15.0 Hz, 2H), 0.89-0.75 (m, 7H).

MS (ESI +) m / z 413 (M + H) ⁺

Example  7: N- (4- (4- ( Cyclohexanesulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclohexanesulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 439 (M + H) ⁺

Example  8: N- (4- (4-((2- Fluoroethyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((2-fluoroethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.73 (s, 1H), 7.86 (s, 1H), 7.61 (d, J = 8.1 Hz, 2H), 7.42 (d, J = 8.5 Hz, 1H), 7.37 (t, J = 2.9 Hz, 1H), 6.89 (d, J = 8.8 Hz, 2H), 6.60 (s, 1H), 2.74 (t, J = 7.0 Hz, 2H) , 2.02 (d, J = 7.9 Hz, 1H), 1.24 (s, 2H), 0.93-0.76 (m, 4H).

MS (ESI +) m / z 403 (M + H) ⁺

Example  9: N- (4- (4-((1,1- Dioxydotetrahydro -2H- Thiopyran )-4- Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1,1-dioxidotetrahydro-2H-thiopyran) -4- synthesis of sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 489 (M + H) ⁺

Example  10: N- (4- (4-((1,1- Dioxydotetrahydrothiophene ) -3- Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1,1-dioxidotetrahydrothiophene) -3-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.61 (s, 1H), 10.41 (s, 1H), 8.00 (s, 1H), 7.75-7.66 (m, 2H), 7.44-7.34 (m, 3H), 6.54 (dd, J = 1.9, 3.7 Hz, 1H), 4.30-4.19 (m, 1H), 3.52 (dd, J = 9.4, 14.0 Hz, 1H), 3.27-3.18 ( m, 2H), 2.43-2.33 (m, 1H), 2.03 (d, J = 7.4 Hz, 1H), 0.81 (dt, J = 4.3, 9.9 Hz, 4H).

MS (ESI < + >) m / z 475 (M + H) ⁺

Example  11: N- (4- (4-((1,1- Dioxydothiethane ) -3- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((1,1-dioxidothietane) -3-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (d, J = 6.0 Hz, 1H), 10.49 (d, J = 13.3 Hz, 1H), 8.01 (d, J = 3.0 Hz, 1H), 7.78-7.69 (m, 2H), 7.46-7.36 (m, 3H), 6.58-6.48 (m, 2H), 4.68-4.57 (m, 2H), 4.52-4.40 (m, 2H) , 2.03 (s, 2H), 0.83-0.76 (m, 4H)

MS (ESI +) m / z 461 (M + H) ⁺

Example  12: N- (4- (4-((6- Chloropyridine ) -3- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((6- chloropyridine ) -3-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.78 (s, 1H), 10.59 (s, 1H), 8.79 (d, J = 2.6 Hz, 1H), 8.19 (dd, J = 2.6, 8.5 Hz, 1H), 7.96 (s, 1H), 7.76 (d, J = 8.5 Hz, 1H), 7.64 (d, J = 8.1 Hz, 2H), 7.38 (t, J = 3.0 Hz, 1H), 7.28 (d, J = 8.3 Hz, 2H), 6.49 (d, J = 3.4 Hz, 1H), 2.03 (s, 1H), 0.86-0.75 (m, 4H)

MS (ESI +) m / z 468, 480 (M + H) ⁺

Example  13: N- (4- (4-((4- Fluorophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((4-fluorophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.56 (d, J = 15.6 Hz, 2H), 7.94 (s, 1H), 7.92-7.83 (m, 2H), 7.60 ( d, J = 8.3 Hz, 2H), 7.46-7.34 (m, 3H), 7.25 (d, J = 8.5 Hz, 2H), 6.48 (dd, J = 1.9, 3.7 Hz, 1H), 2.02 (d, J = 8.7 Hz, 1H), 0.80 (q, J = 5.9, 8.6 Hz, 4H)

MS (ESI +) m / z 451 (M + H) ⁺

Example  14: N- (4- (4-((4- Chlorophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((4-chlorophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.58 (s, 2H), 7.94 (s, 1H), 7.87-7.75 (m, 2H), 7.62 (dd, J = 8.2 , 18.3 Hz, 4H), 7.37 (t, J = 3.1 Hz, 1H), 7.24 (d, J = 8.2 Hz, 2H), 6.48 (dd, J = 1.9, 3.6 Hz, 1H), 2.02 (d, J = 9.2 Hz, 1H), 0.79 (t, J = 7.2 Hz, 4H).

MS (ESI +) m / z 467, 469 (M + H) ⁺

Example  15: N- (4- (4-((1- methyl -1H-imidazole) -5- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((1-methyl-1H-imidazole) -5-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.58 (s, 1H), 10.45 (s, 1H), 7.92 (d, J = 22.8 Hz, 2H), 7.75 (s, 1H), 7.59 (d, J = 8.4 Hz, 2H), 7.37 (t, J = 3.0 Hz, 1H), 7.31 (d, J = 8.2 Hz, 2H), 6.50 (s, 1H), 3.67 (s, 3H), 2.03 (s, 1H), 0.85-0.76 (m, 4H).

MS (ESI +) m / z 437 (M + H) ⁺

Example  16: N- (4- (4-((1- methyl -1H- Pyrazole )-4- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((1-methyl-1H-pyrazole) -4-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.59 (s, 1H), 10.36 (s, 1H), 8.29 (s, 1H), 7.97 (s, 1H), 7.75 ( s, 1H), 7.63 (d, J = 8.3 Hz, 2H), 7.38 (t, J = 3.0 Hz, 1H), 7.34-7.25 (m, 2H), 6.51 (dd, J = 1.9, 3.7 Hz, 1H ), 3.84 (s, 3H), 2.04 (d, J = 7.0 Hz, 1H), 0.80 (tt, J = 3.8, 10.6 Hz, 4H).

MS (ESI +) m / z 437 (M + H) ⁺

Example 17: 4 -(N- (4- (6- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) sulfamoyl) benzamide (4- (N- (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl) sulfamoyl) benzamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.62 (s, 1H), 10.59 (s, 1H), 8.11 (s, 1H), 7.99 (d, J = 8.2 Hz, 2H), 7.93 (s, 1H), 7.89 (d, J = 8.1 Hz, 2H), 7.61 (d, J = 8.5 Hz, 2H), 7.57 (s, 1H), 7.39-7.34 (m, 1H), 7.28 (d, J = 8.3 Hz, 2H), 6.47 (d, J = 3.0 Hz, 1H), 2.03 (s, 1H), 0.84-0.76 (m, 4H).

MS (ESI +) m / z 476 (M + H) ⁺

Example  18: N- (4- (4-((1- Acetylpiperidine )-4- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((1-acetylpiperidine) -4-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, CDCl ₃ ) δ 8.55 (s, 1H), 8.26 (s, 1H), 8.17 (s, 1H), 7.73 (d, J = 8.1 Hz, 2H), 7.34 (d, J = 8.2 Hz, 2H), 6.81 (s, 1H), 6.62 (d, J = 3.1 Hz, 1H), 4.72 (d, J = 12.9 Hz, 1H), 3.93 (d, J = 14.0 Hz, 1H), 3.49 (s, 3H), 3.28 (d, J = 12.3 Hz, 1H), 3.06 (t, J = 12.9 Hz, 1H), 2.55 (t, J = 12.5 Hz, 1H), 2.15 (d, J = 9.9 Hz , 2H), 2.09 (s, 3H), 1.85 (d, J = 12.2 Hz, 2H), 1.13 (d, J = 3.9 Hz, 3H), 0.95-0.78 (m, 9H).

MS (ESI +) m / z 482 (M + H) ⁺

Example  19: N- (4- (4-((4- Isopropoxyphenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((4-isopropoxyphenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.58 (s, 2H), 7.95-7.84 (m, 3H), 7.59 (d, J = 8.2 Hz, 2H), 7.39- 7.19 (m, 6H), 6.54-6.38 (m, 1H), 2.03 (s, 1H), 0.85-0.77 (m, 4H).

MS (ESI +) m / z 491 (M + H) ⁺

Example  20: N- (4- (4-((4- Bromophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((4-bromophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 7.93 (s, 1H), 7.72 (dd, J = 8.0, 5.5 Hz, 4H), 7.55 ( d, J = 8.5 Hz, 2H), 7.39-7.33 (m, 1H), 7.18 (d, J = 8.6 Hz, 2H), 6.53-6.44 (m, 1H), 2.03 (s, 1H), 0.86-0.74 (m, 4 H).

MS (ESI +) m / z 512 (M + H) ⁺

Example  21: N- (4- (4-((4- Cyanophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((4-cyanophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.67 (s, 1H), 10.59 (s, 1H), 8.03-7.84 (m, 5H), 7.61 (d, J = 8.3 Hz, 2H), 7.39-7.23 (m, 3H), 6.48 (s, 1H), 2.03 (s, 1H), 0.82-0.75 (m, 4H).

MS (ESI +) m / z 458 (M + H) ⁺

Example  22: N- (4- (4-((2,3- Dihydrobenzofuran ) -5- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((2,3-dihydrobenzofuran) -5-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.58 (s, 1H), 10.36 (s, 1H), 7.94 (s, 1H), 7.68 (s, 1H), 7.63- 7.55 (m, 3H), 7.40-7.32 (m, 1H), 7.29-7.21 (m, 2H), 6.88 (d, J = 8.4 Hz, 1H), 6.52-6.43 (m, 1H), 4.60 (t, J = 8.7 Hz, 2H), 3.22 (t, J = 8.8 Hz, 2H), 2.03 (s, 1H), 0.84-0.74 (m, 4H).

MS (ESI < + >) m / z 475 (M + H) ⁺

Example  23: N- (4- (4-((6- Methoxypyridine ) -3- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((6- methoxypyridine ) -3-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.59 (s, 2H), 8.64-8.54 (m, 1H), 8.07-7.92 (m, 2H), 7.63 (d, J = 8.1 Hz, 2H), 7.39-7.26 (m, 3H), 7.00 (d, J = 8.6 Hz, 1H), 6.49 (s, 1H), 3.89 (s, 4H), 2.03 (s, 1H), 0.82 0.75 (m, 4 H).

MS (ESI < + >) m / z 464 (M + H) ⁺

Example  24: N- (4- (4- ( Phenylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  (N- (4- (4- ( phenylsulfonamido ) phenyl ) -1H- pyrrolo [2,3- b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (d, J = 7.6 Hz, 1H), 10.55 (d, J = 22.8 Hz, 2H), 7.93 (s, 1H), 7.89-7.80 (m, 2H), 7.69-7.54 (m, 5H), 7.40-7.34 (m, 1H), 7.27 (d, J = 8.7 Hz, 2H), 6.53-6.38 (m, 1H), 2.02 (d, J = 8.1 Hz , 1H), 0.80 (q, J = 8.4, 6.4 Hz, 4H).

MS (ESI +) m / z 433 (M + H) ⁺

Example  25: N- (4- (4-((3- Fluorophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((3-fluorophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.60 (d, J = 19.3 Hz, 2H), 7.94 (s, 1H), 7.71-7.57 (m, 5H), 7.49 ( t, J = 7.5 Hz, 1H), 7.41-7.33 (m, 1H), 7.31-7.16 (m, 2H), 6.56-6.43 (m, 1H), 2.03 (d, J = 9.3 Hz, 1H), 0.87 0.65 (m, 4 H).

MS (ESI +) m / z 451 (M + H) ⁺

Example  26: N- (4- (4-((3- Chlorophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((3-chlorophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 7.94-7.77 (m, 2H), 7.68 (d, J = 7.8 Hz, 1H), 7.58 (dd, J = 6.6, 4.3 Hz, 2H), 7.51-7.43 (m, 1H), 7.36 (t, J = 7.9 Hz, 1H), 7.28-7.18 (m, 4H), 6.58 (d, J = 3.6 Hz, 1H), 1.89 (tt, J = 8.6, 4.6 Hz, 1H), 1.09-1.01 (m, 3H), 0.92 (dq, J = 7.8, 4.1 Hz, 2H), 0.87-0.72 (m, 4H).

MS (ESI +) m / z 467, 469 (M + H) ⁺

Example  27: N- (4- (4-((4- Methylphenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4- methylphenyl ) sulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.33 (s, 1H), 10.46 (s, 1H), 7.87 (s, 1H), 7.62 (d, J = 7.9 Hz, 2H), 7.32 (dd, J = 19.4, 5.6 Hz, 3H), 7.18 (d, J = 7.9 Hz, 2H), 6.94 (d, J = 8.3 Hz, 2H), 6.56-6.44 (m, 1H), 2.29 (s, 3H), 2.00 (d, J = 11.3 Hz, 1H), 0.88-0.66 (m, 4H).

MS (ESI +) m / z 447 (M + H) ⁺

Example  28: N- (4- (4-((4- ( Methylthio Phenyl) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4- (methylthio) phenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.31 (s, 1H), 10.44 (s, 1H), 7.86 (s, 1H), 7.74-7.55 (m, 2H), 7.30 (dd, J = 14.1 , 5.6 Hz, 3H), 7.26-7.15 (m, 2H), 6.90 (d, J = 8.4 Hz, 2H), 6.64-6.31 (m, 1H), 2.02 (s, 1H), 0.89-0.68 (m, 4H).

MS (ESI +) m / z 479 (M + H) ⁺

Example  29: N- (4- (4- (4- ( Ethylsulfonamido )-2- Methylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido )-2- methylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d6) δ 11.48 (s, 1H), 10.63 (s, 1H), 9.86 (s, 1H), 7.75 (s, 1H), 7.54-7.06 (m, 6H), 6.09 (s, 1H), 3.16 (q, J = 7.6 Hz, 3H), 2.14 (s, 3H), 2.04 (s, 1H), 1.23 (t, J = 7.5 Hz, 4H), 0.78 (d, J = 9.5 Hz, 4H).

MS (ESI +) m / z 399 (M + H) ⁺

Example  30: N- (4- (4- (4- ( Ethylsulfonamido )-2- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) -2-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.63 (s, 1H), 10.26 (s, 1H), 7.94 (s, 1H), 7.56 (t, J = 8.4 Hz, 1H), 7.45-7.32 (m, 1H), 7.17 (d, J = 11.3 Hz, 2H), 6.38-6.26 (m, 1H), 3.23 (q, J = 7.2 Hz, 2H), 2.04 (s, 1H ), 1.23 (t, J = 7.2 Hz, 3H), 0.92-0.71 (m, 4H).

MS (ESI +) m / z 403 (M + H) ⁺

Example  31: N- (4- (4-((4- Bromo -3- Fluorophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4-bromo-3-fluorophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.52 (s, 1H), 7.91 (s, 1H), 7.83 (t, J = 7.6 Hz, 1H), 7.65 (dd, J = 2.0, 8.5 Hz, 1H), 7.57-7.44 (m, 3H), 7.33 (t, J = 2.9 Hz, 1H), 7.10 (d, J = 8.4 Hz, 2H), 6.56-6.44 (m, 1H ), 2.02 (s, 1 H), 0.86-0.72 (m, 4H).

MS (ESI +) m / z 529, 531 (M + H) ⁺

Example  32: N- (4- (4-((4- Bromo -2- Fluorophenyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4-bromo-2-fluorophenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.32 (s, 1H), 10.45 (s, 1H), 7.87 (s, 1H), 7.69 (t, J = 8.0 Hz, 1H), 7.54-7.42 ( m, 1H), 7.42-7.24 (m, 4H), 6.96-6.82 (m, 2H), 6.57-6.42 (m, 1H), 2.00 (d, J = 12.5 Hz, 1H), 0.87-0.68 (m, 4H).

MS (ESI +) m / z 529, 531 (M + H) ⁺

Example  33: N- (4- (4-((4-chloro-3- (trifluoromethyl) phenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Cyclopropanecarboxamide (N- (4- (4-((4-chloro-3- (trifluoromethyl) phenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.70 (s, 1H), 10.59 (s, 1H), 8.13 (d, J = 2.3 Hz, 1H), 8.10-8.03 ( m, 1H), 7.96 (d, J = 7.7 Hz, 2H), 7.64 (d, J = 8.2 Hz, 2H), 7.49-7.35 (m, 1H), 7.27 (d, J = 8.3 Hz, 2H), 6.53-6.40 (m, 1H), 2.02 (d, J = 8.5 Hz, 1H), 0.85-0.70 (m, 4H).

MS (ESI +) m / z 535, 537 (M + H) ⁺

Example  34: N- (4- (4- (benzo [d] [1,3] dioxol-5-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclo Propanecarboxamide (N- (4- (4- (benzo [d] [1,3] dioxole-5-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.59 (s, 1H), 10.40 (s, 1H), 7.94 (s, 1H), 7.61 (d, J = 8.3 Hz, 2H), 7.37 (dd, J = 5.7, 2.7 Hz, 2H), 7.27 (dd, J = 5.3, 3.2 Hz, 3H), 7.05 (d, J = 7.8 Hz, 1H), 6.49 (s, 1H), 6.14 (s, 2H), 2.10-1.92 (m, 2H), 1.24 (s, 5H), 0.86-0.70 (m, 5H).

MS (ESI +) m / z 477 (M + H) ⁺

Example  35: N- (4- (4- (ethylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) -2-methylcyclopropane-1-carboxamide (N Synthesis of-(4- (4- (ethylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) -2-methylcyclopropane-1-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.59 (s, 1H), 10.02 (s, 1H), 7.96 (d, J = 5.8 Hz, 1H), 7.69 (dd, J = 4.1, 8.6 Hz, 2H), 7.47 (d, J = 7.8 Hz, 1H), 7.39 (dd, J = 4.4, 7.5 Hz, 3H), 7.11 (d, J = 7.9 Hz, 1H), 6.63- 6.49 (m, 1H), 3.17 (q, J = 7.3 Hz, 2H), 1.86-1.74 (m, 1H), 1.34-1.17 (m, 5H), 1.17-0.93 (m, 4H).

MS (ESI +) m / z 399 (M + H) ⁺

Example  36: N- (4- (4-(((4-fluorophenyl) methyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide Synthesis of (N- (4- (4-(((4-fluorophenyl) methyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 465 (M + H) ⁺

Example  37: N- (4- (4-((4- ( N, N - Dimethyl sulfamoyl Phenyl) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4- (N, N-dimethylsulfamoyl) phenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

MS (ESI +) m / z 540 (M + H) ⁺

Example  38: N- (4- (4-((2,3- Dihydrobenzo [b] [1,4] dioxin ) -6- Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((2,3-dihydrobenzo [b] [1,4] Synthesis of dioxine) -6-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.58 (s, 1H), 7.94 (s, 1H), 7.60 (s, 2H), 7.27 (s, 5H), 7.01 ( s, 2H), 6.49 (s, 1H), 4.28 (s, 4H), 2.03 (s, 1H), 0.80 (s, 4H).

MS (ESI +) m / z 491 (M + H) ⁺

Example  39: N- (4- (4-((4- (1H-) Tetrazole -1-yl) phenyl) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4- (1H-tetrazol-1-yl) phenyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.58 (s, 1H), 10.39 (s, 1H), 8.12 (d, J = 21.2 Hz, 1H), 7.94 (s, 1H), 7.74 (d, J = 8.7 Hz, 1H), 7.61 (t, J = 9.0 Hz, 2H), 7.39-7.00 (m, 6H), 6.48 (s, 1H), 2.03 (s, 1H), 0.80 (s, 4 H).

MS (ESI +) m / z 501 (M + H) ⁺

Example  40: N- (4- (4-((6- Cyanopyridine ) -3- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((6- cyanopyridine ) -3-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (d, J = 19.4 Hz, 1H), 10.56 (d, J = 12.4 Hz, 1H), 9.00 (d, J = 55.6 Hz, 1H), 8.46 -7.81 (m, 4H), 7.56 (d, J = 37.7 Hz, 2H), 7.41-7.11 (m, 3H), 6.48 (d, J = 8.3 Hz, 1H), 2.02 (s, 1H), 0.79 ( s, 4H).

MS (ESI +) m / z 459 (M + H) ⁺

Example  41: N- (4- (4-((1- Methylethyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((1- methylethyl ) sulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 9.96 (s, 1H), 7.99 (s, 1H), 7.67 (d, J = 8.2 Hz, 2H), 7.39 (d, J = 6.8 Hz, 3H), 6.54 (s, 1H), 2.04 (s, 1H), 1.30-1.24 (m, 6H), 0.81 (s, 4H).

MS (ESI +) m / z 399 (M + H) ⁺

Example  42: N- (4- (4-((1-ethylpropyl)) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((1-ethylpropyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.62 (s, 1H), 10.04 (s, 1H), 7.99 (s, 1H), 7.70-7.62 (m, 2H), 7.41-7.34 (m, 3H), 6.54 (dd, J = 3.5, 1.8 Hz, 1H), 2.97 (dd, J = 8.7, 3.7 Hz, 1H), 2.03 (d, J = 5.0 Hz, 1H), 1.87 (ddd, J = 14.7, 7.6, 5.1 Hz, 2H), 1.70 (dt, J = 14.3, 7.2 Hz, 2H), 0.96 (t, J = 7.5 Hz, 6H), 0.80 (t, J = 5.5 Hz, 4H).

MS (ESI +) m / z 427 (M + H) ⁺

Example  43: N- (4- (4-((2- Methylpropyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((2-methylpropyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 10.00 (s, 1H), 8.00 (s, 1H), 7.69 (d, J = 8.7 Hz, 2H), 7.37 (t, J = 9.9 Hz, 3H), 6.55 (s, 1H), 3.06 (d, J = 6.8 Hz, 2H), 2.17 (s, 1H), 2.04 (s, 1H), 1.05- 0.95 (m, 6H), 0.81 (s, 4H).

MS (ESI +) m / z 413 (M + H) ⁺

Example  44: N- (4- (4-((2,2- Dimethylpropyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((2,2-dimethylpropyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 9.99 (s, 1H), 8.00 (s, 1H), 7.69 (d, J = 6.8 Hz, 2H), 7.44-7.29 (m, 3H), 6.55 (s, 1H), 3.11 (s, 2H), 2.04 (s, 1H), 1.11 (q, J = 7.5, 5.8 Hz, 9H), 0.81 (s , 4H).

MS (ESI +) m / z 427 (M + H) ⁺

Example  45: N- (4- (4-((3- Methylbutyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((3- methylbutyl ) sulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 10.00 (s, 1H), 8.00 (s, 1H), 7.69 (d, J = 8.4 Hz, 2H), 7.37 (d, J = 9.7 Hz, 3H), 6.53 (s, 1H), 3.14 (d, J = 8.8 Hz, 2H), 2.04 (s, 1H), 1.60 (s, 3H), 0.82 ( s, 10 H).

MS (ESI +) m / z 427 (M + H) ⁺

Example  46: N- (4- (4-(( Cyclopropylmethyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((cyclopropylmethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 10.06 (s, 1H), 7.99 (s, 1H), 7.74-7.61 (m, 2H), 7.38 (d, J = 8.9 Hz, 3H), 6.54 (s, 1H), 3.21-3.07 (m, 2H), 2.04 (s, 1H), 1.02 (s, 1H), 0.81 (s, 4H), 0.56 (s, 2H), 0.27 (s, 2H).

MS (ESI +) m / z 411 (M + H) ⁺

Example  47: N- (4- (4-((cyclohexylmethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4 Synthesis of-(4-((cyclohexylmethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 10.01 (s, 1H), 8.00 (s, 1H), 7.68 (d, J = 7.9 Hz, 2H), 7.37 (t, J = 10.1 Hz, 3H), 6.54 (s, 1H), 3.11-2.99 (m, 2H), 2.03 (s, 1H), 1.85 (s, 2H), 1.63 (s, 2H ), 1.24 (s, 2H), 1.06 (s, 2H), 0.81 (s, 4H).

MS (ESI +) m / z 453 (M + H) ⁺

Example  48: N- (4- (4- ( Allylsulfon Amido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  (N- (4- (4- ( allylsulfonamido ) phenyl ) -1H- pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.63 (s, 1H), 10.12 (s, 1H), 8.00 (s, 1H), 7.69 (d, J = 8.3 Hz, 2H), 7.38 (dd, J = 8.2, 5.6 Hz, 3H), 6.55 (dd, J = 3.7, 1.9 Hz, 1H), 5.81 (ddd, J = 17.2, 10.1, 7.3 Hz, 1H), 5.36 (dd , J = 19.3, 13.6 Hz, 2H), 3.98 (d, J = 7.2 Hz, 2H), 2.04 (s, 1H), 0.85-0.76 (m, 4H).

MS (ESI +) m / z 397 (M + H) ⁺

Example  49: N- (4- (4-(( Fluoromethyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-(( fluoromethyl ) sulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (s, 2H), 8.00 (s, 1H), 7.69 (d, J = 8.1 Hz, 2H), 7.38 (d, J = 11.9 Hz, 3H), 6.54 (s, 1H), 5.59 (s, 1H), 5.48 (s, 1H), 2.05 (s, 1H), 0.81 (s, 4H).

MS (ESI +) m / z 389 (M + H) ⁺

Example  50: N- (4- (4-(( Difluoromethyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((difluoromethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 11.16 (s, 1H), 10.62 (s, 1H), 8.01 (s, 1H), 7.72 (d, J = 8.6 Hz, 2H), 7.50-7.30 (m, 3H), 7.14 (d, J = 51.5 Hz, 1H), 6.53 (s, 1H), 2.05 (s, 1H), 0.92-0.71 (m, 4H).

MS (ESI +) m / z 407 (M + H) ⁺

Example  51: N- (4- (4-((2,2-difluoroethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane Carboxamide  Synthesis of (N- (4- (4-((2,2-difluoroethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.36 (s, 1H), 10.48 (s, 1H), 7.92 (s, 1H), 7.44 (s, 2H), 7.32 (s, 1H), 6.70 ( s, 2H), 6.54 (s, 1H), 5.40 (s, 2H), 4.03 (s, 1H), 2.03 (s, 1H), 0.79 (d, J = 14.6 Hz, 4H).

MS (ESI +) m / z 421 (M + H) ⁺

Example  52: N- (4- (4-((3- Cyanopropyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((3-cyanopropyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.60 (s, 1H), 10.22-9.95 (m, 1H), 8.00 (s, 1H), 7.70 (d, J = 8.1 Hz, 2H), 7.39 (s, 3H), 6.54 (s, 1H), 3.24 (d, J = 6.7 Hz, 2H), 2.67 (t, J = 7.4 Hz, 2H), 2.02 (d, J = 12.0 Hz, 3H), 0.81 (s, 4H).

MS (ESI +) m / z 424 (M + H) ⁺

Example  53: N- (4- (4-((2- Ethoxyethyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((2-ethoxyethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 9.89 (s, 1H), 8.01 (d, J = 15.2 Hz, 1H), 7.68 (d, J = 8.9 Hz, 2H), 7.48-7.29 (m, 3H), 6.54 (s, 1H), 3.83-3.68 (m, 2H), 3.49-3.39 (m, 4H), 2.05 (s, 1H), 1.13 0.98 (m, 3H), 0.91-0.73 (m, 4H).

MS (ESI +) m / z 429 (M + H) ⁺

Example  54: N- (4- (4-(((tetrahydrofuran-3-yl) methyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  Synthesis of (N- (4- (4-(((tetrahydrofuran-3-yl) methyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (s, 1H), 9.93 (s, 1H), 8.00 (s, 1H), 7.80-7.63 (m, 2H), 7.38 (d, J = 11.3 Hz, 3H), 6.55 (s, 1H), 3.89 (d, J = 10.3 Hz, 1H), 3.66 (d, J = 29.1 Hz, 2H), 2.09 (d, J = 20.8 Hz, 2H), 1.64 (d, J = 12.5 Hz, 1H), 0.82 (s, 4H).

MS (ESI +) m / z 441 (M + H) ⁺

Example  55: N- (4- (4-((( Tetrahydro -2H-pyran-4-yl) methyl ) Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((tetrahydro-2H-pyran-4-yl) methyl) synthesis of sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.62 (d, J = 12.6 Hz, 1H), 9.93 (s, 1H), 8.00 (s, 1H), 7.68 (d, J = 9.5 Hz, 2H), 7.51-7.22 (m, 3H), 6.55 (d, J = 11.0 Hz, 1H), 3.81 (s, 2H), 3.14 (q, J = 6.7 Hz, 2H), 2.09 ( d, J = 30.9 Hz, 2H), 1.76 (s, 2H), 1.32 (s, 2H), 0.82 (s, 4H).

MS (ESI +) m / z 455 (M + H) ⁺

Example  56: N- (4- (4-((2- ( Methylsulfonyl )ethyl) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((2- (methylsulfonyl) ethyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

MS (ESI +) m / z 463 (M + H) ⁺

Example  57: N- (4- (4- ( Cyclopropanesulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclopropanesulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 9.94 (s, 1H), 8.00 (s, 1H), 7.68 (dd, J = 11.1, 4.7 Hz, 2H), 7.40 (d, J = 8.1 Hz, 3H), 6.54 (s, 1H), 2.71 (s, 1H), 2.04 (s, 1H), 0.97 (d, J = 9.6 Hz, 4H), 0.80 (d, J = 12.4 Hz, 4H).

MS (ESI +) m / z 397 (M + H) ⁺

Example  58: N- (4- (4- ( Cyclobutanesulfone Amido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclobutanesulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (s, 1H), 9.93 (s, 1H), 7.99 (s, 1H), 7.70-7.64 (m, 2H), 7.39 (dd, J = 3.5, 2.5 Hz, 1H), 7.35 (d, J = 8.6 Hz, 2H), 6.53 (dd, J = 3.6, 1.9 Hz, 1H), 3.99 (p, J = 8.0 Hz, 1H ), 2.32 (d, J = 18.7 Hz, 2H), 2.20 (dt, J = 8.4, 4.4 Hz, 2H), 2.02 (d, J = 13.0 Hz, 1H), 1.95-1.82 (m, 2H), 0.81 (d, J = 4.4 Hz, 4H).

MS (ESI +) m / z 411 (M + H) ⁺

Example  59: N- (4- (3- Cyano -4-( Ethylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3- cyano -4-( ethylsulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 410 (M + H) ⁺

Example  60: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl )-One- methyl -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (ethylsulfonamido) -3-fluorophenyl) -1-methyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.77 (d, J = 19.2 Hz, 1H), 8.06 (d, J = 14.7 Hz, 1H), 7.69-7.46 (m, 4H), 6.57 (dd, J = 3.7, 1.8 Hz, 1H), 3.82 (d, J = 4.9 Hz, 3H), 2.08 (s, 1H), 1.27 (dt, J = 18.9, 7.1 Hz, 5H), 0.86-0.80 (m, 4H ).

MS (ESI +) m / z 417 (M + H) ⁺

Example  61: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1-propyl-1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  Synthesis of (N- (4- (4- (ethylsulfonamido) -3-fluorophenyl) -1-propyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.72 (s, 1H), 8.07 (s, 1H), 7.68-7.50 (m, 4H), 6.59 (d, J = 3.6 Hz, 1H), 4.20 ( t, J = 7.3 Hz, 2H), 3.60 (t, J = 7.0 Hz, 3H), 2.10 (s, 1H), 1.84 (q, J = 7.2 Hz, 2H), 1.42 (q, J = 7.5 Hz, 2H), 1.31-1.27 (m, 3H), 0.84-0.78 (m, 4H).

MS (ESI +) m / z 445 (M + H) ⁺

Example  62: N- (1- ( Cyanomethyl ) -4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (1- (cyanomethyl) -4- (4- (ethylsulfonamido) -3-fluorophenyl) -1H- Synthesis of pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.88 (d, J = 15.7 Hz, 1H), 9.86 (s, 1H), 8.14 (d, J = 12.2 Hz, 1H), 7.70-7.48 (m, 4H), 6.70 (d, J = 3.8 Hz, 1H), 5.43 (d, J = 4.2 Hz, 2H), 2.12 (s, 1H), 1.28 (d, J = 6.7 Hz, 3H), 1.23 (s, 2H), 0.85-0.81 (m, 4H).

MS (ESI +) m / z 442 (M + H) ⁺

Example  63: N- (4- (3- Chloro -4-( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (3-chloro-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.63 (s, 1H), 10.70 (s, 1H), 9.65 (s, 1H), 8.02 (s, 1H), 7.76 (d, J = 2.0 Hz, 1H), 7.70 (dd, J = 2.0, 8.4 Hz, 1H), 7.63 (d, J = 8.4 Hz, 1H), 7.45 (dd, J = 2.5, 3.6 Hz, 1H), 6.53 (dd, J = 1.8 , 3.5 Hz, 1H), 3.20-3.12 (m, 2H), 2.03 (q, J = 5.9, 7.3 Hz, 1H), 1.84-1.74 (m, 2H), 0.99 (t, J = 7.4 Hz, 3H) , 0.85-0.75 (m, 4H).

MS (ESI < + >) m / z 433, 435 (M + H) ⁺

Example  64: N- (4- (4- ( Ethylsulfonamido ) -3- Methylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) -3- methylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.56 (s, 1H), 10.65 (s, 1H), 9.21 (s, 1H), 8.00 (s, 1H), 7.58-7.50 (m, 2H), 7.50-7.38 (m, 2H), 6.54 (dd, J = 1.9, 3.5 Hz, 1H), 3.15 (q, J = 7.3 Hz, 2H), 2.41 (s, 3H), 2.08-1.97 (m, 1H) , 1.28 (t, J = 7.3 Hz, 3H), 0.89-0.74 (m, 4H).

MS (ESI +) m / z 399 (M + H) ⁺

Example  65: N- (4- (3- methyl -4-( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.64 (s, 1H), 9.11 (s, 1H), 8.00 (s, 1H), 7.58-7.50 (m, 2H), 7.47-7.37 (m, 2H), 6.54 (dd, J = 1.9, 3.5 Hz, 1H), 3.16-3.06 (m, 2H), 2.39 (s, 3H), 2.09-1.99 (m, 1H), 1.76 ( q, J = 7.5 Hz, 2H), 0.99 (t, J = 7.4 Hz, 3H), 0.87-0.75 (m, 4H).

MS (ESI +) m / z 413 (M + H) ⁺

Example  66: N- (4- (3- Fluoro -4-( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.68 (s, 1H), 9.84 (s, 1H), 8.02 (s, 1H), 7.62-7.52 (m, 3H), 7.49-7.40 (m, 1H), 6.56 (dd, J = 3.5, 1.8 Hz, 1H), 3.23-3.10 (m, 2H), 2.08-1.97 (m, 1H), 1.84-1.71 (m, 2H), 0.99 (t, J = 7.4 Hz, 3H), 0.80 (dd, J = 10.1, 3.5 Hz, 4H).

MS (ESI +) m / z 417 (M + H) ⁺

Example  67: N- (4- (4- ( Butyl sulfon amido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( butylsulfonamido ) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.59 (s, 1H), 10.65 (s, 1H), 9.82 (s, 1H), 8.02 (s, 1H), 7.62-7.53 (m, 3H), 7.43 (t, J = 3.0 Hz, 1H), 6.56 (dd, J = 3.5, 1.8 Hz, 1H), 3.21-3.13 (m, 2H), 2.11-1.98 (m, 1H), 1.73 (p, J = 7.7 Hz, 2H), 1.41 (q, J = 7.4 Hz, 2H), 0.89 (d, J = 7.3 Hz, 3H), 0.83-0.76 (m, 4H).

MS (ESI +) m / z 431 (M + H) ⁺

Example  68: N- (4- (4- ( Cyclohexanesulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-ylcyclopropanecarboxamide (N- (4- (4- (cyclohexanesulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.59 (s, 1H), 10.65 (s, 1H), 9.78 (s, 1H), 8.02 (s, 1H), 7.60 (t, J = 8.4 Hz, 1H ), 7.54 (dd, J = 8.7, 4.7 Hz, 2H), 7.43 (d, J = 5.8 Hz, 1H), 6.56 (dd, J = 3.4, 1.7 Hz, 1H), 3.06 (t, J = 11.8 Hz , 1H), 2.12 (d, J = 12.3 Hz, 2H), 2.05 (s, 1H), 1.79 (d, J = 12.7 Hz, 2H), 1.62 (d, J = 13.0 Hz, 1H), 1.44 (q , J = 12.4 Hz, 2H), 1.34-1.25 (m, 2H), 1.15 (t, J = 12.7 Hz, 1H), 0.84-0.77 (m, 4H).

MS (ESI +) m / z 457 (M + H) ⁺

Example  69: N- (4- (4- ( Cyclopropanesulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4- (cyclopropanesulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.59 (s, 1H), 10.65 (s, 1H), 9.80 (s, 1H), 8.01 (s, 1H), 7.58 (dt, J = 11.8, 6.9 Hz , 3H), 7.43 (d, J = 5.9 Hz, 1H), 6.56 (dd, J = 3.5, 1.8 Hz, 1H), 2.74 (td, J = 7.8, 3.8 Hz, 1H), 2.08-1.98 (m, 1H), 1.01-0.93 (m, 4H), 0.83-0.79 (m, 4H).

MS (ESI +) m / z 415 (M + H) ⁺

Example  70: N- (4- (4-(( Cyclohexylmethyl ) Sulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((cyclohexylmethyl) sulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.62 (s, 1H), 10.69 (s, 1H), 9.87 (s, 1H), 8.02 (s, 1H), 7.60-7.52 (m, 3H), 7.44 (t, J = 3.1 Hz, 1H), 6.56 (dd, J = 3.6, 1.8 Hz, 1H), 3.07 (d, J = 6.0 Hz, 2H), 2.04 (s, 1H), 1.89 (t, J = 14.8 Hz, 3H), 1.62 (dd, J = 27.0, 12.4 Hz, 3H), 1.30-0.97 (m, 7H), 0.86-0.75 (m, 4H)

MS (ESI +) m / z 471 (M + H) ⁺

Example  71: N- (4- (4- ( Allylsulfon Amido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( allylsulfonamido ) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.62 (s, 1H), 10.69 (s, 1H), 9.92 (s, 1H), 8.02 (s, 1H), 7.58 (dd, J = 16.4, 8.0 Hz, 3H), 7.44 (t, J = 2.9 Hz, 1H), 6.56 (d, J = 4.7 Hz, 1H), 5.86 (td, J = 17.1, 7.2 Hz, 1H), 5.50-5.37 (m, 2H ), 3.99 (d, J = 7.2 Hz, 2H), 2.06-1.99 (m, 1H), 0.81 (d, J = 4.8 Hz, 4H)

MS (ESI +) m / z 415 (M + H) ⁺

Example  72: N- (4- (3- Fluoro -4-(((tetrahydrofuran-3-yl) methyl ) Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4-(((tetrahydrofuran-3-yl) methyl) synthesis of sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.68 (s, 1H), 9.96 (s, 1H), 8.02 (s, 1H), 7.64-7.52 (m, 3H), 7.44 (dd, J = 3.5, 2.5 Hz, 1H), 6.56 (dd, J = 3.6, 1.8 Hz, 1H), 3.88 (dd, J = 8.6, 7.2 Hz, 1H), 3.72 (td, J = 8.3, 5.0 Hz, 1H), 3.63 (d, J = 7.8 Hz, 1H), 2.70-2.61 (m, 1H), 2.17-2.07 (m, 1H), 2.06-1.97 (m, 1H), 1.68 (dq, J = 12.3, 7.7 Hz, 1H), 0.83-0.78 (m, 4H)

MS (ESI +) m / z 459 (M + H) ⁺

Example  73: N- (4- (3- Fluoro -4-((( Tetrahydro -2H-pyran-4-yl) methyl ) Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4-(((tetrahydro-2H-pyran-4- Synthesis of yl) methyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.62 (s, 1H), 10.69 (s, 1H), 9.91 (s, 1H), 8.03 (s, 1H), 7.62-7.53 (m, 3H), 7.46-7.41 (m, 1H), 6.56 (dd, J = 3.5, 1.8 Hz, 1H), 3.85-3.76 (m, 2H), 3.28 (dd, J = 11.7, 2.0 Hz, 2H), 3.16 (d, J = 6.4 Hz, 2H), 2.18 (q, J = 6.0, 4.1 Hz, 1H), 2.03 (d, J = 8.7 Hz, 1H), 1.78 (d, J = 13.0 Hz, 2H), 1.35 (qd, J = 12.2, 4.4 Hz, 2H), 0.84-0.75 (m, 4H)

MS (ESI +) m / z 473 (M + H) ⁺

Example  74: N- (4- (4- ( Ethylsulfonamido ) Phenyl) -2- methyl -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) phenyl )-2- methyl -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 399 (M + H) ⁺

Example  75: N- (4- (3- Fluoro -4-((2- Methylpropyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4-((2-methylpropyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.68 (s, 1H), 8.02 (s, 1H), 7.62-7.50 (m, 3H), 7.44 (dd, J = 3.5 , 2.5 Hz, 1H), 6.56 (dd, J = 3.5, 1.8 Hz, 1H), 3.08 (d, J = 6.4 Hz, 2H), 2.21 (dq, J = 13.3, 6.6 Hz, 1H), 2.04 (h , J = 6.2, 5.4 Hz, 1H), 1.04 (d, J = 6.7 Hz, 6H), 0.83-0.78 (m, 4H)

MS (ESI +) m / z 431 (M + H) ⁺

Example  76: N- (4- (3- Fluoro -4-((3- Fluoropropyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4-((3-fluoropropyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.62 (s, 1H), 10.68 (s, 1H), 9.98 (s, 1H), 8.02 (s, 1H), 7.61-7.54 (m, 3H), 7.44 (t, J = 3.0 Hz, 1H), 6.56 (dd, J = 3.6, 1.8 Hz, 1H), 4.62 (t, J = 5.9 Hz, 1H), 4.50 (t, J = 6.0 Hz, 1H), 3.28 (d, J = 15.4 Hz, 2H), 2.12 (ddd, J = 33.0, 16.5, 9.7 Hz, 3H), 0.83-0.78 (m, 4H)

MS (ESI +) m / z 435 (M + H) ⁺

Example  77: N- (4- (4-((3- Cyanopropyl ) Sulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((3-cyanopropyl) sulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.62 (s, 1H), 10.68 (s, 1H), 10.03 (s, 1H), 8.02 (s, 1H), 7.61-7.55 (m, 3H), 7.44 (dd, J = 3.5, 2.5 Hz, 1H), 6.56 (dd, J = 3.5, 1.8 Hz, 1H), 3.30-3.24 (m, 2H), 2.70 (t, J = 7.3 Hz, 2H), 2.06 (p, J = 7.2 Hz, 3H), 0.85-0.77 (m, 4H)

MS (ESI +) m / z 442 (M + H) ⁺

Example  78: N- (4- (4- ( Cyclobutanesulfone Amido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4- (cyclobutanesulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.68 (s, 1H), 9.77 (s, 1H), 8.02 (s, 1H), 7.62-7.50 (m, 3H), 7.44 (t, J = 3.0 Hz, 1H), 6.55 (t, J = 2.5 Hz, 1H), 4.00 (t, J = 8.1 Hz, 1H), 2.42-1.82 (m, 6H), 0.81 (t, J = 6.5 Hz, 4H)

MS (ESI +) m / z 429 (M + H) ⁺

Example  79: N- (4- (4-((2,2- Dimethylpropyl ) Sulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((2,2-dimethylpropyl) sulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.68 (s, 1H), 8.02 (s, 1H), 7.62-7.51 (m, 3H), 7.44 (t, J = 2.8 Hz, 1H), 6.57 (s, 1H), 3.14 (s, 2H), 2.03 (d, J = 12.4 Hz, 1H), 1.11 (s, 9H), 0.81 (d, J = 4.6 Hz, 4H)

MS (ESI +) m / z 445 (M + H) ⁺

Example  80: N- (4- (4-(( Cyclopropylmethyl ) Sulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((cyclopropylmethyl) sulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.67 (s, 1H), 9.88 (s, 1H), 8.01 (s, 1H), 7.60 (t, J = 8.4 Hz, 1H), 7.53 (t, J = 8.4 Hz, 2H), 7.43 (t, J = 3.0 Hz, 1H), 6.56 (d, J = 3.2 Hz, 1H), 3.14 (d, J = 7.0 Hz, 2H) , 2.04 (s, 1H), 1.08 (s, 1H), 0.87-0.74 (m, 4H), 0.56 (q, J = 5.8 Hz, 2H), 0.34 (q, J = 5.1 Hz, 2H)

MS (ESI +) m / z 429 (M + H) ⁺

Example  81: N- (4- (4- ( Ethylsulfonamido ) -3,5- Difluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ), 3,5-difluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.69 (s, 1H), 10.73 (s, 1H), 9.64 (s, 1H), 8.03 (s, 1H), 7.53-7.42 (m, 3H), 6.58 (dd, J = 1.8, 3.5 Hz, 1H), 3.19 (q, J = 7.4 Hz, 2H), 2.09-1.99 (m, 1H), 1.34 (t, J = 7.3 Hz, 3H), 0.83-0.77 (m, 4H)

MS (ESI +) m / z 421 (M + H) ⁺

Example  82: N- (4- (3,5- Difluoro -4-( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3,5-difluoro-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.68 (s, 1H), 10.73 (s, 1H), 9.64 (s, 1H), 8.03 (s, 1H), 7.51-7.45 (m, 3H), 6.58 (dd, J = 1.8, 3.6 Hz, 1H), 3.21-3.12 (m, 2H), 2.04 (dd, J = 5.7, 11.3 Hz, 1H), 1.83 (q, J = 7.6 Hz, 2H), 1.02 (t, J = 7.4 Hz, 3H), 0.86-0.78 (m, 4H).

MS (ESI +) m / z 435 (M + H) ⁺

Example  83: N- (4- (4- ( Ethylsulfonamido ) -2,5- Difluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) -2,5-difluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.69 (s, 1H), 10.12 (s, 1H), 7.96 (s, 1H), 7.54-7.46 (m, 1H), 7.45-7.38 (m, 2H), 6.32 (d, J = 2.1 Hz, 1H), 3.23 (q, J = 7.3 Hz, 2H), 2.03 (d, J = 5.8 Hz, 1H), 1.26 (q, J = 7.8, 8.3 Hz, 4H), 0.84-0.75 (m, 4H)

MS (ESI +) m / z 421 (M + H) ⁺

Example  84: N- (4- (2,5- Difluoro -4-( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (2,5-difluoro-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.70 (s, 1H), 10.12 (s, 1H), 7.97 (s, 1H), 7.50 (dd, J = 6.7, 10.6 Hz, 1H), 7.46-7.37 (m, 2H), 6.32 (d, J = 2.6 Hz, 1H), 3.25-3.17 (m, 2H), 2.09-1.98 (m, 1H), 1.75 (dt, J = 7.6, 15.2 Hz, 2H), 0.99 (t, J = 7.4 Hz, 3H), 0.85-0.78 (m, 4H)

MS (ESI +) m / z 435 (M + H) ⁺

Example  85: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido ) -3- Fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) -3-fluorophenyl)- 1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.67 (s, 1H), 10.18 (s, 1H), 8.01 (s, 1H), 7.56 (d, J = 13.3 Hz, 3H), 7.43 (s, 1H), 6.55 (s, 1H), 2.02 (s, 1H), 1.33 (d, J = 42.9 Hz, 2H), 1.23 (s, 2H), 0.81 (s, 4H)

MS (ESI +) m / z 454 (M + H) ⁺

Example  86: N- (4- (4-(((1- ( Cyanomethyl ) Cyclopropyl ) methyl ) Sulfonamido ) -3- Fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1- (cyanomethyl) cyclopropyl) methyl) sulfonamido) -3- Synthesis of fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 468 (M + H) ⁺

Example  87: N- (4- (4-((3- Cyano -3- Methylbutyl ) Sulfonamido ) -3- Fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3-cyano-3-methylbutyl) sulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.68 (s, 1H), 10.03 (s, 1H), 8.02 (s, 1H), 7.57 (t, J = 5.9 Hz, 3H), 7.44 (s, 1H), 6.59-6.49 (m, 1H), 2.06 (d, J = 12.8 Hz, 5H), 1.23 (s, 6H), 0.85-0.77 (m, 4H)

MS (ESI +) m / z 470 (M + H) ⁺

Example  88: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.62 (s, 1H), 7.99 (s, 1H), 7.68 (d, J = 8.5 Hz, 2H), 7.41-7.32 ( m, 3H), 6.53 (dd, J = 3.5, 1.8 Hz, 1H), 3.54 (s, 2H), 2.06-1.94 (m, 2H), 1.36 (q, J = 4.9 Hz, 2H), 1.20-1.14 (m, 2H), 0.83-0.75 (m, 4H)

MS (ESI +) m / z 436 (M + H) ⁺

Example  89: N- (4- (4-(((1- ( Cyanomethyl ) Cyclopropyl ) methyl ) Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1- (cyanomethyl) cyclopropyl) methyl) sulfonamido) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.52 (s, 1H), 10.62 (s, 1H), 10.23 (s, 1H), 7.99 (s, 1H), 7.69 (d, J = 8.5 Hz, 2H), 7.42-7.31 (m, 3H), 6.54 (dd, J = 3.6, 1.8 Hz, 1H), 3.30 (s, 2H), 2.86 (s, 2H), 2.09-1.92 (m, 1H), 0.80 (td, J = 7.9, 2.9 Hz, 4H), 0.75-0.63 (m, 4H)

MS (ESI +) m / z 450 (M + H) ⁺

Example  90: N- (4- (4- ( Cyclopropanesulfonamido )-2- Methylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclopropanesulfonamido ) -2-methylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.47 (s, 1H), 10.62 (s, 1H), 9.80 (s, 1H), 7.77 (s, 1H), 7.33 (dd, J = 3.5, 2.4 Hz , 1H), 7.26-7.15 (m, 3H), 6.08 (dd, J = 3.5, 1.9 Hz, 1H), 2.15 (s, 3H), 2.06-2.00 (m, 1H), 0.99-0.96 (m, 4H ), 0.82 -0.74 (m, 4H)

MS (ESI +) m / z 411 (M + H) ⁺

Example  91: N- (4- (4- ( Cyclobutanesulfone Amido )-2- Methylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclobutanesulfonamido ) -2-methylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.47 (s, 1H), 10.62 (s, 1H), 9.77 (s, 1H), 7.76 (s, 1H), 7.33 (dd, J = 3.5, 2.5 Hz , 1H), 7.25-7.09 (m, 3H), 6.07 (dd, J = 3.5, 1.9 Hz, 1H), 3.99 (p, J = 8.1 Hz, 1H), 2.36 (dd, J = 19.7, 9.4 Hz, 2H), 2.23-2.17 (m, 2H), 2.13 (s, 3H), 2.03 (s, 1H), 1.95-1.84 (m, 2H), 0.82-0.74 (m, 4H)

MS (ESI +) m / z 425 (M + H) ⁺

Example  92: N- (4- (4-(( Cyclopropylmethyl ) Sulfonamido )-2- Methylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((cyclopropylmethyl) sulfonamido) -2-methylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

¹ H NMR (400 MHz, Chloroform-d) δ 11.47 (s, 1H), 10.61 (s, 1H), 9.91 (s, 1H), 7.76 (s, 1H), 7.33 (d, J = 2.4 Hz, 1H ), 7.28-7.10 (m, 3H), 6.08 (dd, J = 3.5, 1.9 Hz, 1H), 3.13 (d, J = 7.1 Hz, 2H), 2.14 (s, 3H), 2.07-1.94 (m, 1H), 1.02 (td, J = 7.5, 3.8 Hz, 1H), 0.78 (dd, J = 8.4, 2.5 Hz, 4H), 0.58-0.53 (m, 2H), 0.28 (dt, J = 6.3, 4.5 Hz , 2H)

MS (ESI +) m / z 425 (M + H) ⁺

Example  93: N- (4- (4- ( Ethylsulfonamido ) Phenyl) -3- methyl -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) phenyl ) -3- methyl -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.17 (s, 1H), 10.56 (s, 1H), 7.72 (s, 1H), 7.42-7.38 (m, 2H), 7.31 (d, J = 6.8 Hz , 2H), 7.10 (s, 1H), 3.15 (q, J = 7.2 Hz, 2H), 2.03 (s, 1H), 1.87 (s, 3H), 1.24-1.20 (m, 5H), 0.81-0.74 ( m, 4H)

MS (ESI +) m / z 399 (M + H) ⁺

Example  94: N- (3- methyl -4- (4- ( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (3-methyl-4- (4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.17 (d, J = 2.4 Hz, 1H), 10.57 (s, 1H), 7.72 (s, 1H), 7.39 (d, J = 8.5 Hz, 2H), 7.34-7.28 (m, 3H), 7.10 (d, J = 2.1 Hz, 1H), 3.12 (t, J = 2.1 Hz, 2H), 2.02 (d, J = 2.1 Hz, 1H), 1.86 (s, 3H ), 1.74-1.70 (m, 2H), 0.95 (d, J = 7.5 Hz, 3H), 0.81-0.73 (m, 4H)

MS (ESI +) m / z 413 (M + H) ⁺

Example  95: N- (4- (2- methyl -4-( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (2-methyl-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.48 (s, 1H), 10.62 (s, 1H), 9.84 (s, 1H), 7.77 (s, 1H), 7.33 (dd, J = 3.5, 2.5 Hz , 1H), 7.23 (s, 1H), 7.19-7.10 (m, 2H), 6.08 (dd, J = 3.5, 1.8 Hz, 1H), 3.16-3.11 (m, 2H), 2.14 (s, 3H), 2.09-2.01 (m, 1H), 1.72 (h, J = 7.5 Hz, 2H), 0.97 (t, J = 7.4 Hz, 3H), 0.83-0.73 (m, 4H)

MS (ESI +) m / z 413 (M + H) ⁺

Example  96: N- (4- (4-((3- Cyanopropyl ) Sulfonamido )-2- Methylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((3-cyanopropyl) sulfonamido) -2-methylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, Chloroform-d) δ 11.47 (s, 1H), 10.62 (s, 1H), 7.76 (s, 1H), 7.37-7.31 (m, 1H), 7.24 (t, J = 7.1 Hz , 1H), 7.20-7.14 (m, 2H), 6.11-6.04 (m, 1H), 3.25 (dd, J = 8.5, 6.6 Hz, 2H), 2.68 (t, J = 7.3 Hz, 2H), 2.14 ( s, 3H), 2.04-1.98 (m, 2H), 1.92 (d, J = 8.2 Hz, 1H), 0.82-0.74 (m, 4H)

MS (ESI +) m / z 438 (M + H) ⁺

Example 97: 6 -( Cyclopropanecarboxamido ) -4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H-pyrrolo [2,3-b] pyridine 7- Oxide  (6- ( cyclopropanecarboxamido ) -4- (4- (ethylsulfonamido) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridine 7- oxide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 12.54 (s, 1H), 10.78 (s, 1H), 9.84 (s, 1H), 8.16 (s, 1H), 7.61-7.50 (m, 3H), 7.46 (t, J = 2.8 Hz, 1H), 6.71 (dd, J = 3.5, 1.8 Hz, 1H), 3.18 (q, J = 7.2 Hz, 2H), 2.41 (q, J = 6.5, 5.3 Hz, 1H ), 1.28 (t, J = 7.3 Hz, 3H), 0.89 (d, J = 7.9 Hz, 4H)

MS (ESI +) m / z 419 (M + H) ⁺

Example  98: N- (4- (4- ( Ethylsulfonamido ) -3- ( Trifluoromethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (ethylsulfonamido) -3- (trifluoromethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.64 (s, 1H), 10.32 (s, 1H), 7.82 (s, 1H), 7.67 (d, J = 2.2 Hz, 1H), 7.60-7.52 (m, 1H), 7.43 (d, J = 8.4 Hz, 1H), 7.34-7.26 (m, 1H), 6.01 (dd, J = 3.6, 1.8 Hz, 1H), 3.24 (d , J = 7.4 Hz, 2H), 2.07-1.98 (m, 1H), 1.25 (t, J = 7.3 Hz, 3H), 0.81-0.72 (m, 4H)

MS (ESI +) m / z 453 (M + H) ⁺

Example  99: N- (4- (2-ethyl-4- ( Ethylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (2- ethyl -4-( ethylsulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (s, 1H), 10.61 (s, 1H), 9.85 (s, 1H), 7.77 (s, 1H), 7.32 (dd, J = 3.5, 2.4 Hz, 1H), 7.24-7.12 (m, 3H), 6.05 (dd, J = 3.5, 1.9 Hz, 1H), 3.16 (q, J = 7.3 Hz, 2H), 2.46 (d, J = 7.6 Hz, 2H ), 2.11-1.97 (m, 1H), 1.23 (t, J = 7.3 Hz, 3H), 0.95 (t, J = 7.5 Hz, 3H), 0.81-0.72 (m, 4H)

MS (ESI +) m / z 413 (M + H) ⁺

Example  100: N- (4- (3- Fluoro -2- methyl -4-( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-2-methyl-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.66 (s, 1H), 9.70 (s, 1H), 7.79 (s, 1H), 7.36 (dd, J = 5.4, 2.5 Hz, 2H), 7.12 (d, J = 8.4 Hz, 1H), 6.16-6.08 (m, 1H), 3.19-3.09 (m, 2H), 2.08 (d, J = 2.6 Hz, 3H), 2.05-2.01 (m, 1H), 1.83-1.73 (m, 2H), 1.00 (t, J = 7.2 Hz, 3H), 0.84-0.74 (m, 4H)

MS (ESI +) m / z 431 (M + H) ⁺

Example  101: N- (4- (4- ( Ethylsulfonamido ) -3- Fluoro -2- Methylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (ethylsulfonamido) -3-fluoro-2-methylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.66 (s, 1H), 9.71 (s, 1H), 7.79 (s, 1H), 7.40-7.30 (m, 2H), 7.18-7.06 (m, 1H), 6.11 (dd, J = 3.5, 1.9 Hz, 1H), 3.16 (t, J = 7.3 Hz, 2H), 2.08 (d, J = 2.7 Hz, 3H), 2.03-1.95 (m, 1H), 1.29 (t, J = 7.3 Hz, 3H), 0.82-0.73 (m, 4H)

MS (ESI +) m / z 417 (M + H) ⁺

Example  102: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido )-2- Methylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) -2-methylphenyl)- 1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (s, 1H), 10.61 (s, 1H), 9.91 (s, 1H), 7.76 (s, 1H), 7.33 (dd, J = 3.5, 2.4 Hz, 1H), 7.23 (d, J = 8.3 Hz, 1H), 7.18 (d, J = 2.2 Hz, 1H), 7.14 (dd, J = 8.1, 2.3 Hz, 1H), 6.07 (dd, J = 3.5 , 1.9 Hz, 1H), 3.52 (s, 2H), 2.14 (s, 3H), 1.99 (dt, J = 14.0, 7.8 Hz, 2H), 1.38-1.33 (m, 2H), 1.22-1.16 (m, 2H), 0.80-0.74 (m, 4H)

MS (ESI +) m / z 450 (M + H) ⁺

Example  103: N- (4- (4-(((1- ( Cyanomethyl ) Cyclopropyl ) methyl ) Sulfonamido )-2- Methylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1- (cyanomethyl) cyclopropyl) methyl) sulfonamido) -2- Synthesis of methylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (s, 1H), 10.61 (s, 1H), 7.76 (s, 1H), 7.32 (dd, J = 3.4, 2.4 Hz, 1H), 7.24 ( d, J = 8.3 Hz, 1H), 7.17-7.11 (m, 2H), 2.86 (s, 2H), 2.14 (s, 3H), 2.05-1.95 (m, 2H), 0.79 (d, J = 3.8 Hz , 2H), 0.75-0.65 (m, 4H)

MS (ESI < + >) m / z 464 (M + H) ⁺

Example  104: N- (4- (4-((3- Cyanopropyl ) Sulfonamido ) -2,5- Difluorophenyl ) -1H-pyrrolo [2,3-b] pyridin 6-yl) Cyclopropanecarboxamide  Synthesis of (N- (4- (4-((3-cyanopropyl) sulfonamido) -2,5-difluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.64 (s, 1H), 10.69 (s, 1H), 7.96 (d, J = 1.2 Hz, 1H), 7.52 (dd, J = 6.6, 10.6 Hz, 1H), 7.47-7.39 (m, 4H), 6.31 (dt, J = 2.0, 3.9 Hz, 1H), 3.37 (s, 2H), 2.70 (t, J = 7.3 Hz, 2H), 2.11-1.99 (m , 3H), 0.85-0.76 (m, 4H)

MS (ESI +) m / z 460 (M + H) ⁺

Example  105: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido ) -2,5- Difluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) -2,5-difluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.58 (s, 1H), 10.67 (s, 1H), 7.96 (s, 1H), 7.47 (ddd, J = 6.8, 11.0, 15.3 Hz, 2H), 7.40 (dd, J = 2.5, 3.5 Hz, 1H), 6.31 (dd, J = 1.9, 3.6 Hz, 1H), 3.62 (s, 2H), 2.07-2.00 (m, 1H), 1.38 (q, J = 4.1, 4.8 Hz, 2H), 1.30-1.22 (m, 2H), 0.84-0.75 (m, 4H)

MS (ESI +) m / z 472 (M + H) ⁺

Example  106: N- (4- (4-(((1- ( Cyanomethyl ) Cyclopropyl ) methyl ) Sulfonamido ) -2,5-difluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1- (cyanomethyl ) cyclopropyl) methyl) sulfonamido) -2,5-difluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 486 (M + H) ⁺

Example  107: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido ) -3,5- Difluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) -3,5-difluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 472 (M + H) ⁺

Example  108: N- (4- (4-(((1- ( Cyanomethyl ) Cyclopropyl ) methyl ) Sulfonamido ) -3,5-difluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1- (cyanomethyl ) cyclopropyl) methyl) sulfonamido) -3,5-difluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.68 (s, 1H), 10.71 (s, 1H), 8.03 (s, 1H), 7.52-7.44 (m, 3H), 6.58 (dd, J = 1.8 , 3.5 Hz, 1H), 3.38 (s, 2H), 2.86 (s, 2H), 2.04 (td, J = 3.8, 7.4, 7.8 Hz, 1H), 0.93-0.87 (m, 2H), 0.82 (ddd, J = 2.3, 6.2, 9.5 Hz, 4H), 0.74-0.68 (m, 2H)

MS (ESI +) m / z 486 (M + H) ⁺

Example  109: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido )-2- Ethylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) -2-ethylphenyl)- 1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.63 (s, 1H), 10.23 (s, 1H), 7.77 (s, 1H), 7.32 (s, 1H), 7.25- 7.09 (m, 3H), 6.04 (d, J = 3.2 Hz, 1H), 3.52 (s, 2H), 2.04 (d, J = 14.3 Hz, 1H), 1.36 (s, 2H), 1.20 (d, J = 5.2 Hz, 2H), 0.95 (t, J = 7.6 Hz, 3H), 0.77 (d, J = 7.3 Hz, 4H)

MS (ESI < + >) m / z 464 (M + H) ⁺

Example  110: N- (4- (4-(((1- ( Cyanomethyl ) Cyclopropyl ) methyl ) Sulfonamido )-2- Ethylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1- (cyanomethyl) cyclopropyl) methyl) sulfonamido) -2- Synthesis of ethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.63 (s, 1H), 10.08 (s, 1H), 7.77 (s, 1H), 7.32 (s, 1H), 7.19 ( d, J = 10.0 Hz, 2H), 7.12 (d, J = 8.6 Hz, 1H), 6.04 (s, 1H), 2.85 (s, 2H), 2.03 (s, 1H), 0.95 (t, J = 7.6 Hz, 3H), 0.78 (s, 4H), 0.73 (s, 2H), 0.66 (s, 2H)

MS (ESI +) m / z 478 (M + H) ⁺

Example  111: N- (4- (4-((3- Cyanopropyl ) Sulfonamido )-2- Ethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((3-cyanopropyl) sulfonamido) -2-ethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.64 (s, 1H), 10.01 (s, 1H), 7.78 (s, 1H), 7.32 (s, 1H), 7.18 ( dd, J = 23.0, 9.1 Hz, 3H), 6.05 (s, 1H), 3.25 (t, J = 7.9 Hz, 2H), 2.68 (t, J = 7.3 Hz, 2H), 2.02 (q, J = 7.5 Hz, 3H), 0.96 (t, J = 7.5 Hz, 3H), 0.77 (d, J = 7.7 Hz, 4H)

MS (ESI +) m / z 452 (M + H) ⁺

Example  112: N- (4- (4- ( Cyclohexanesulfonamido )-2- Ethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclohexanesulfonamido ) -2-ethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.65 (s, 1H), 9.86 (d, J = 13.7 Hz, 1H), 7.79 (s, 1H), 7.41-7.07 ( m, 4H), 6.05 (s, 1H), 3.06 (s, 1H), 2.06 (s, 3H), 1.77 (s, 2H), 1.59 (s, 1H), 1.34 (d, J = 77.0 Hz, 3H ), 1.17-1.05 (m, 1H), 0.93-0.81 (m, 5H)

MS (ESI +) m / z 467 (M + H) ⁺

Example  113: N- (4- (4- ( Cyclopropanesulfonamido )-2- Ethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclopropanesulfonamido ) -2-ethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.64 (s, 1H), 9.82 (s, 1H), 7.78 (s, 1H), 7.32 (d, J = 3.1 Hz, 1H), 7.25 (s, 1H), 7.18 (s, 2H), 6.04 (d, J = 3.0 Hz, 1H), 3.38 (d, J = 6.4 Hz, 1H), 2.74-2.65 (m, 1H), 2.04 (d, J = 6.9 Hz, 1H), 1.09 (t, J = 7.2 Hz, 1H), 0.97 (d, J = 7.2 Hz, 7H), 0.82-0.74 (m, 4H)

MS (ESI +) m / z 425 (M + H) ⁺

Example  114: N- (4- (4- ( Cyclobutanesulfone Amido )-2- Ethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclobutanesulfonamido ) -2-ethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.64 (s, 1H), 9.78 (s, 1H), 7.77 (s, 1H), 7.32 (s, 1H), 7.14 ( dd, J = 24.3, 10.7 Hz, 3H), 6.04 (s, 1H), 4.06-3.91 (m, 1H), 2.46 (s, 2H), 2.39-2.30 (m, 2H), 2.20 (s, 2H) , 2.07-1.98 (m, 1H), 1.93 (dd, J = 19.3, 10.2 Hz, 2H), 0.94 (t, J = 7.6 Hz, 3H), 0.82-0.73 (m, 4H)

MS (ESI +) m / z 439 (M + H) ⁺

Example  115: N- (4- (2-ethyl-4- ( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (2- ethyl -4-( propylsulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.64 (s, 1H), 9.87 (s, 1H), 7.78 (s, 1H), 7.32 (s, 1H), 7.16 ( dd, J = 22.3, 9.1 Hz, 3H), 6.05 (s, 1H), 3.13 (t, J = 7.4 Hz, 2H), 2.42 (s, 2H), 2.02 (d, J = 7.2 Hz, 1H), 1.72 (q, J = 7.7 Hz, 2H), 0.96 (q, J = 7.8, 7.1 Hz, 6H), 0.82-0.74 (m, 4H)

MS (ESI +) m / z 427 (M + H) ⁺

Example  116: N- (4- (4- ( Butyl sulfon amido )-2- Ethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( butylsulfonamido )-2- ethylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.63 (s, 1H), 9.87 (s, 1H), 7.78 (s, 1H), 7.32 (d, J = 3.1 Hz, 1H), 7.16 (dd, J = 22.4, 9.6 Hz, 3H), 6.04 (d, J = 2.9 Hz, 1H), 3.14 (t, J = 7.9 Hz, 2H), 2.42 (t, J = 7.3 Hz, 2H), 2.04 (d, J = 5.7 Hz, 1H), 1.69 (q, J = 8.0 Hz, 2H), 1.38 (q, J = 7.6 Hz, 2H), 0.94 (q, J = 6.1, 4.6 Hz, 3H), 0.84 (t, J = 7.4 Hz, 3H), 0.81-0.75 (m, 4H)

MS (ESI +) m / z 441 (M + H) ⁺

Example  117: N- (4- (2- methyl -4-((4,4,4- Trifluorobutyl ) Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (2-methyl-4-((4,4,4-trifluorobutyl) sulfonamido ) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.64 (s, 1H), 7.77 (s, 1H), 7.38-7.29 (m, 1H), 7.25 (d, J = 8.2 Hz, 1H), 7.21-7.11 (m, 2H), 6.07 (dd, J = 1.8, 3.5 Hz, 1H), 3.28 (t, J = 7.7 Hz, 2H), 2.47-2.35 (m, 2H), 2.14 (s, 3H), 1.99 (d, J = 33.4 Hz, 1H), 1.91 (dd, J = 5.7, 8.6 Hz, 2H), 0.83-0.74 (m, 4H)

MS (ESI +) m / z 481 (M + H) ⁺

Example  118: N- (4- (4- ( Cyclopropanesulfonamido )-2-( Trifluoromethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Cyclopropanecarboxamide  Synthesis of (N- (4- (4- (cyclopropanesulfonamido) -2- (trifluoromethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.67 (s, 1H), 10.30 (s, 1H), 7.83 (s, 1H), 7.69 (t, J = 1.7 Hz, 1H), 7.59 (d, J = 8.4 Hz, 1H), 7.44 (d, J = 8.4 Hz, 1H), 7.33 (t, J = 2.6 Hz, 1H), 6.00 (dt, J = 3.4, 1.6 Hz, 1H), 2.80 (p, J = 6.5 Hz, 1H), 2.06-1.96 (m, 1H), 1.04-0.95 (m, 4H), 0.77 (d, J = 6.5 Hz, 4H)

MS (ESI +) m / z 465 (M + H) ⁺

Example  119: N- (4- (4- ( Propylsulfonylamido )-2-( Trifluoromethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (propylsulfonamido) -2- (trifluoromethyl) phenyl) -1H-pyrrolo Synthesis of [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.67 (s, 1H), 10.34 (s, 1H), 7.83 (s, 1H), 7.65 (s, 1H), 7.56 ( d, J = 8.5 Hz, 1H), 7.43 (d, J = 8.4 Hz, 1H), 7.32 (d, J = 2.5 Hz, 1H), 6.04-5.98 (m, 1H), 3.22 (t, J = 7.6 Hz, 2H), 2.05-1.98 (m, 1H), 1.73 (q, J = 7.7 Hz, 2H), 1.02-0.91 (m, 3H), 0.77 (d, J = 6.4 Hz, 4H)

MS (ESI +) m / z 467 (M + H) ⁺

Example  120: N- (4- (4- (cyclobutanesulfonamido) -2- (trifluoromethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarbox Synthesis of amide (N- (4- (4- (cyclobutanesulfonamido) -2- (trifluoromethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.67 (s, 1H), 10.26 (s, 1H), 7.82 (s, 1H), 7.65 (s, 1H), 7.54 ( d, J = 8.3 Hz, 1H), 7.42 (d, J = 8.3 Hz, 1H), 7.33 (d, J = 3.3 Hz, 1H), 6.00 (t, J = 2.2 Hz, 1H), 4.08 (p, J = 8.2 Hz, 1H), 2.35 (p, J = 9.7 Hz, 2H), 2.22 (s, 2H), 2.02 (d, J = 6.4 Hz, 1H), 1.98-1.83 (m, 2H), 0.77 ( d, J = 6.3 Hz, 4H)

MS (ESI +) m / z 479 (M + H) ⁺

Example  121: N- (4- (4-((3,4- Difluorophenyl ) Sulfonamido )-2-( Trifluoromethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3,4-difluorophenyl) sulfonamido) -2- (trifluoromethyl ) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.63 (s, 1H), 7.84 (s, 1H), 7.76 (s, 1H), 7.67 (s, 2H), 7.46 ( s, 1H), 7.30 (s, 3H), 5.93 (s, 1H), 2.01 (s, 1H), 0.77 (s, 4H)

MS (ESI +) m / z 537 (M + H) ⁺

Example  122: N- (4- (4-((3- Fluorophenyl ) Sulfonamido )-2-( Trifluoromethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3-fluorophenyl) sulfonamido) -2- (trifluoromethyl) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.97 (s, 1H), 10.65 (s, 1H), 7.76 (s, 1H), 7.68 (s, 2H), 7.63 ( d, J = 8.6 Hz, 1H), 7.57 (d, J = 8.8 Hz, 1H), 7.53 (s, 1H), 7.46 (d, J = 8.6 Hz, 1H), 7.38 (d, J = 8.3 Hz, 1H), 7.31 (d, J = 3.2 Hz, 1H), 5.90 (s, 1H), 2.06-1.95 (m, 1H), 0.81-0.73 (m, 4H)

MS (ESI +) m / z 519 (M + H) ⁺

Example  123: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido ) -3- Ethylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) -3-ethylphenyl)- 1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.56 (s, 1H), 10.64 (s, 1H), 9.47 (s, 1H), 8.01 (s, 1H), 7.59 (d, J = 2.0 Hz, 1H), 7.52 (dd, J = 8.3, 2.1 Hz, 1H), 7.45 (d, J = 8.2 Hz, 1H), 7.41 (t, J = 3.0 Hz, 1H), 6.52 (dd, J = 3.6, 1.8 Hz, 1H), 3.54 (s, 2H), 2.81 (q, J = 7.5 Hz, 2H), 2.09-1.98 (m, 1H), 1.40 (q, J = 4.8, 3.9 Hz, 2H), 1.29 (t , J = 3.7 Hz, 2H), 1.22 (t, J = 7.5 Hz, 3H), 0.86-0.73 (m, 4H)

MS (ESI < + >) m / z 464 (M + H) ⁺

Example  124: N- (4- (3-ethyl-4- ( Ethylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3- ethyl -4-( ethylsulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.64 (s, 1H), 9.18 (s, 1H), 8.01 (s, 1H), 7.59 (d, J = 2.1 Hz, 1H), 7.53 (dd, J = 8.2, 2.1 Hz, 1H), 7.45-7.39 (m, 2H), 6.52 (dd, J = 3.5, 1.8 Hz, 1H), 3.17 (q, J = 7.3 Hz, 2H ), 2.81 (q, J = 7.5 Hz, 2H), 2.04 (d, J = 7.0 Hz, 1H), 1.30 (t, J = 7.3 Hz, 3H), 1.22 (t, J = 7.5 Hz, 3H), 0.83-0.78 (m, 4H)

MS (ESI +) m / z 413 (M + H) ⁺

Example  125: N- (4- (4- ( Cyclopropanesulfonamido ) -3- Ethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclopropanesulfonamido ) -3-ethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.64 (s, 1H), 9.22 (s, 1H), 8.02 (s, 1H), 7.59 (d, J = 2.0 Hz, 1H), 7.55-7.47 (m, 2H), 7.41 (dd, J = 3.5, 2.5 Hz, 1H), 6.53 (dd, J = 3.6, 1.9 Hz, 1H), 2.84 (q, J = 7.5 Hz, 2H ), 2.72-2.67 (m, 1H), 2.03 (t, J = 6.5 Hz, 1H), 1.22 (t, J = 7.5 Hz, 3H), 1.03-0.95 (m, 2H), 0.94-0.89 (m, 2H), 0.84-0.76 (m, 4H)

MS (ESI +) m / z 425 (M + H) ⁺

Example  126: N- (4- (3-ethyl-4- ( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3- ethyl -4-( propylsulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.64 (s, 1H), 9.19 (s, 1H), 8.01 (s, 1H), 7.59 (d, J = 2.1 Hz, 1H), 7.55-7.50 (m, 1H), 7.46-7.38 (m, 2H), 6.53 (dd, J = 3.5, 1.8 Hz, 1H), 3.17-3.09 (m, 2H), 2.81 (q, J = 7.5 Hz, 2H), 2.04 (s, 1H), 1.78 (h, J = 7.4 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H), 1.01 (t, J = 7.5 Hz, 3H), 0.85 0.76 (m, 4H)

MS (ESI +) m / z 427 (M + H) ⁺

Example  127: N- (4- (4- ( Butyl sulfon amido ) -3- Ethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( butylsulfonamido ) -3- ethylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.64 (s, 1H), 9.19 (s, 1H), 8.01 (s, 1H), 7.58 (d, J = 2.1 Hz, 1H), 7.53 (d, J = 8.1 Hz, 1H), 7.45-7.36 (m, 2H), 6.52 (dd, J = 3.5, 1.9 Hz, 1H), 3.18-3.12 (m, 2H), 2.81 (q , J = 7.5 Hz, 2H), 2.04 (s, 1H), 1.72 (q, J = 7.7 Hz, 2H), 1.43 (h, J = 7.3 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H ), 0.89 (t, J = 7.4 Hz, 3H), 0.84-0.76 (m, 4H)

MS (ESI +) m / z 441 (M + H) ⁺

Example  128: N- (4- (4- ( Cyclobutanesulfone Amido ) -3- Ethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclobutanesulfonamido ) -3-ethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.64 (s, 1H), 9.15 (s, 1H), 8.01 (s, 1H), 7.57 (d, J = 2.0 Hz, 1H), 7.51 (dd, J = 8.2, 2.2 Hz, 1H), 7.44-7.34 (m, 2H), 6.52 (dd, J = 3.5, 1.8 Hz, 1H), 3.97 (p, J = 8.2 Hz, 1H ), 2.79 (q, J = 7.5 Hz, 2H), 2.38-2.23 (m, 4H), 2.03 (d, J = 4.8 Hz, 1H), 1.97-1.86 (m, 2H), 1.21 (t, J = 7.5 Hz, 3H), 0.84-0.76 (m, 4H)

MS (ESI +) m / z 439 (M + H) ⁺

Example  129: N- (4- (6- ( Methylsulfonamido )-[1,1'-biphenyl] -3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (6- ( methylsulfonamido )-[1,1'-biphenyl] -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.25 (s, 1H), 10.47 (d, J = 3.2 Hz, 1H), 10.04 (t, J = 2.8 Hz, 1H), 7.68 (d, J = 3.2 Hz, 1H), 7.42-7.28 (m, 3H), 7.17-7.04 (m, 6H), 5.86 (s, 1H), 3.22 (d, J = 6.5 Hz, 2H), 1.98 (d, J = 7.2 Hz, 1H), 1.25 (q, J = 7.0, 5.7 Hz, 3H), 0.74 (d, J = 5.9 Hz, 4H)

MS (ESI +) m / z 447 (M + H) ⁺

Example  130: N- (4- (6- ( Cyclopropanesulfonamido )-[1,1'-biphenyl] -3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (6- (cyclopropanesulfonamido)-[1,1'-biphenyl] -3-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.25 (s, 1H), 10.48 (s, 1H), 9.98 (s, 1H), 7.69 (s, 1H), 7.41-7.30 (m, 3H), 7.19-7.07 (m, 6H), 5.85 (s, 1H), 2.78 (d, J = 7.9 Hz, 1H), 1.98 (d, J = 7.5 Hz, 1H), 1.01 (t, J = 4.6 Hz, 4H ), 0.75 (d, J = 6.1 Hz, 4H)

MS (ESI +) m / z 473 (M + H) ⁺

Example  131: N- (4- (4- ( Ethylsulfonamido ) -2,3- Dimethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) -2,3-dimethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.63 (s, 1H), 9.15 (d, J = 4.1 Hz, 1H), 7.75 (d, J = 4.2 Hz, 1H) , 7.33 (s, 1H), 7.28-7.00 (m, 2H), 6.04 (s, 1H), 3.11 (p, J = 7.4 Hz, 2H), 2.31 (t, J = 2.9 Hz, 3H), 2.07 ( t, J = 2.9 Hz, 3H), 2.03 (s, 1H), 1.29 (dt, J = 11.0, 5.8 Hz, 3H), 0.77 (d, J = 8.2 Hz, 4H)

MS (ESI +) m / z 413 (M + H) ⁺

Example  132: N- (4- (2,3-dimethyl-4- ( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (2,3-dimethyl-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.63 (s, 1H), 9.15 (d, J = 4.4 Hz, 1H), 7.76 (t, J = 3.2 Hz, 1H) , 7.33 (s, 1H), 7.22 (d, J = 7.8 Hz, 1H), 7.10 (t, J = 6.4 Hz, 1H), 6.04 (s, 1H), 3.08 (q, J = 6.4, 4.8 Hz, 2H), 2.30 (d, J = 4.4 Hz, 3H), 2.06 (d, J = 4.1 Hz, 3H), 2.03 (s, 1H), 1.78 (q, J = 7.4 Hz, 2H), 1.01 (t, J = 7.0 Hz, 3H), 0.82-0.76 (m, 4H)

MS (ESI +) m / z 427 (M + H) ⁺

Example  133: N- (4- (4- ( Cyclopropanesulfonamido ) -2,3- Dimethylphenyl ) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4- (cyclopropanesulfonamido) -2,3-dimethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.63 (d, J = 3.3 Hz, 1H), 9.18 (d, J = 3.1 Hz, 1H), 7.76 (d, J = 3.5 Hz, 1H), 7.33 (s, 1H), 7.25 (d, J = 4.5 Hz, 1H), 7.09 (d, J = 8.9 Hz, 1H), 6.03 (s, 1H), 2.64 (s, 1H) , 2.34 (d, J = 2.9 Hz, 3H), 2.07 (d, J = 4.8 Hz, 3H), 0.93 (d, J = 29.3 Hz, 4H), 0.82-0.74 (m, 4H)

MS (ESI +) m / z 425 (M + H) ⁺

Example 134: 6 -( Cyclopropanecarboxamido ) -4- (4- ( Ethylsulfonamido )-2- Methylphenyl ) -1H-pyrrolo [2,3-b] pyridine 7- Oxide (6- ( cyclopropanecarboxamido ) -4- (4- (ethylsulfonamido) -2-methylphenyl) -1H-pyrrolo [2,3-b] pyridine 7- oxide ) Synthesis

MS (ESI +) m / z 415 (M + H) ⁺

Example 135: 6 -( Cyclopropanecarboxamido ) -4- (3-ethyl-4- ( Ethylsulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridine 7- Oxide  (6- ( cyclopropanecarboxamido ) -4- (3-ethyl-4- (ethylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridine 7- oxide ) Synthesis

MS (ESI +) m / z 429 (M + H) ⁺

Example 136: 6 -( Cyclopropanecarboxamido ) -4- (4- ( Cyclopropanesulfonamido ) -2,3-dimethylphenyl) -1H-pyrrolo [2,3-b] pyridine 7- Oxide  (6- (cyclopropanecarboxamido) -4- (4- (cyclopropanesulfonamido) -2,3-dimethylphenyl) -1H-pyrrolo [2,3-b] pyridine 7- oxide ) Synthesis

MS (ESI +) m / z 441 (M + H) ⁺

Example 137: 4 -(4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido )-2- Ethylphenyl ) -6- (cyclo Propanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine  7- Oxide  4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) -2-ethylphenyl) -6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridine 7- oxide  synthesis

MS (ESI +) m / z 480 (M + H) ⁺

Example  138: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido ) -3,5- Diethylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) -3,5-diethylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.57 (s, 1H), 10.97 (s, 1H), 10.65 (s, 1H), 8.23 (s, 1H), 7.53 (s, 2H), 7.11 ( d, J = 7.8 Hz, 1H), 6.58-6.47 (m, 1H), 3.06 (s, 2H), 2.60 (q, J = 7.5 Hz, 4H), 2.05 (s, 1H), 1.40 (d, J = 10.4 Hz, 4H), 1.19 (t, J = 7.5 Hz, 6H), 0.85-0.74 (m, 4H)

MS (ESI +) m / z 492 (M + H) ⁺

Example  139: N- (4- (4-((3,4- Difluorophenyl ) Sulfonamido ) -3,5- Diethylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3,4-difluorophenyl) sulfonamido) -3,5-diethylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.62 (s, 1H), 9.73 (s, 1H), 8.00 (s, 1H), 7.84-7.67 (m, 2H), 7.63 (d, J = 9.6 Hz, 1H), 7.41 (s, 3H), 6.48 (dd, J = 3.6, 1.9 Hz, 1H), 2.05 (d, J = 5.8 Hz, 1H), 1.05 (t, J = 7.5 Hz, 6H), 0.85-0.74 (m, 4H)

MS (ESI +) m / z 525 (M + H) ⁺

Example  140: Methyl2 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -5- (ethylsulfonamido) benzoate ( methyl  2- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) -5- (ethylsulfonamido) benzoate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.60 (s, 1H), 10.19 (s, 1H), 7.79 (s, 1H), 7.66 (s, 1H), 7.50 ( s, 2H), 7.33 (s, 1H), 6.09 (s, 1H), 3.46 (s, 3H), 3.21 (q, J = 7.3 Hz, 2H), 2.04 (s, 1H), 1.23 (t, J = 7.3 Hz, 3H), 0.82-0.75 (m, 4H)

MS (ESI +) m / z 443 (M + H) ⁺

Example  141: Methyl2 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -5- (propylsulfonamido) benzoate ( methyl  2- (6- ( cyclopropanecarboxamido Synthesis of) -1H-pyrrolo [2,3-b] pyridin-4-yl) -5- (propylsulfonamido) benzoate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.60 (s, 1H), 10.19 (s, 1H), 7.79 (s, 1H), 7.65 (t, J = 1.5 Hz, 1H), 7.50 (d, J = 1.5 Hz, 2H), 7.33 (dd, J = 3.5, 2.4 Hz, 1H), 6.09 (dd, J = 3.6, 1.9 Hz, 1H), 3.46 (s, 3H), 3.23-3.10 (m, 2H), 2.08-1.99 (m, 1H), 1.78-1.61 (m, 2H), 0.97 (t, J = 7.4 Hz, 3H), 0.83-0.72 (m, 4H)

MS (ESI +) m / z 457 (M + H) ⁺

Example  142: Methyl5 -(((One- Cyanocyclopropyl ) methyl ) Sulfonamido ) -2- (6- ( Cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) benzoate ( methyl  Synthesis of 5-(((1-cyanocyclopropyl) methyl) sulfonamido) -2- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) benzoate

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.60 (s, 1H), 7.79 (s, 1H), 7.66 (d, J = 1.5 Hz, 1H), 7.49 (d, J = 1.5 Hz, 2H), 7.32 (t, J = 3.0 Hz, 1H), 6.07 (dd, J = 3.5, 1.9 Hz, 1H), 3.59 (s, 2H), 3.45 (s, 3H), 2.03 ( s, 1H), 1.37 (q, J = 4.8 Hz, 2H), 1.20 (q, J = 5.3, 4.9 Hz, 2H), 0.81-0.70 (m, 4H)

MS (ESI +) m / z 494 (M + H) ⁺

Example 143: 5 -(((One- Cyanocyclopropyl ) methyl ) Sulfonamido ) -2- (6- ( Cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) benzoic acid (5-(((1-cyanocyclopropyl) methyl) sulfonamido) -2- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2, 3-b] pyridin-4-yl) benzoic acid ) Synthesis

MS (ESI +) m / z 480 (M + H) ⁺

Example  144: N- (4- (2- Cyano -4-( Ethylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (2- cyano -4-( ethylsulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.64 (s, 1H), 10.72 (s, 1H), 10.40 (s, 1H), 7.98 (s, 1H), 7.75-7.59 (m, 3H), 7.42 (t, J = 3.0 Hz, 1H), 6.27 (dd, J = 3.6, 1.8 Hz, 1H), 3.29 (q, J = 7.3 Hz, 2H), 2.10-1.98 (m, 1H), 1.25 (t , J = 7.3 Hz, 3H), 0.85-0.70 (m, 4H)

MS (ESI +) m / z 410 (M + H) ⁺

Example  145: N- (4- (2- Cyano -4-( Propylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (2-cyano-4- (propylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.64 (s, 1H), 10.72 (s, 1H), 10.39 (s, 1H), 7.98 (s, 1H), 7.70-7.57 (m, 3H), 7.42 (t, J = 3.0 Hz, 1H), 6.27 (dd, J = 3.5, 1.7 Hz, 1H), 3.30-3.23 (m, 2H), 2.10-1.97 (m, 1H), 1.73 (h, J = 7.5 Hz, 2H), 0.98 (t, J = 7.4 Hz, 3H), 0.88-0.68 (m, 4H)

MS (ESI +) m / z 424 (M + H) ⁺

Example  146: N- (4- (2- Cyano -4-((3,4- Difluorophenyl ) Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (2-cyano-4-((3,4-difluorophenyl) sulfonamido) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.64 (s, 1H), 11.04 (s, 1H), 10.71 (s, 1H), 7.97 (d, J = 8.3 Hz, 1H), 7.93 (s, 1H), 7.73 (d, J = 3.5 Hz, 1H), 7.72-7.67 (m, 1H), 7.64-7.60 (m, 2H), 7.54 (dd, J = 8.5, 2.3 Hz, 1H), 7.41 (t , J = 3.0 Hz, 1H), 6.20 (dd, J = 3.6, 1.8 Hz, 1H), 2.09-1.97 (m, 1H), 0.85-0.76 (m, 4H)

MS (ESI +) m / z 494 (M + H) ⁺

Example  147: N- (4- (2- Cyano -4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (2-cyano-4-(((1-cyanocyclopropyl) methyl) sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.64 (s, 1H), 10.78 (s, 1H), 10.72 (s, 1H), 7.98 (s, 1H), 7.70-7.57 (m, 3H), 7.42 (t, J = 3.0 Hz, 1H), 6.25 (t, J = 2.6 Hz, 1H), 3.70 (s, 2H), 2.09-1.98 (m, 1H), 1.09 (t, J = 7.0 Hz, 4H ), 0.83-0.77 (m, 4H)

MS (ESI +) m / z 461 (M + H) ⁺

Example  148: N- (4- (6- ( Ethylsulfonamido Pyridin-3-yl) -1 H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (6- ( ethylsulfonamido ) pyridin -3- yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.78 (s, 1H), 10.68 (s, 1H), 8.57 (s, 1H), 8.08 (dd, J = 2.5, 8.6 Hz, 1H), 8.01 (s, 1H), 7.43 (dd, J = 2.5, 3.5 Hz, 1H), 7.16 (d, J = 8.6 Hz, 1H), 6.54 (dd, J = 1.9, 3.5 Hz, 1H ), 3.52 (s, 2H), 2.04 (t, J = 5.0 Hz, 1H), 1.25 (t, J = 7.3 Hz, 4H), 0.85-0.73 (m, 4H)

MS (ESI +) m / z 386 (M + H) ⁺

Example  149: N- (4- (5- ( Ethylsulfonamido ) -6- Fluoropyridine 2-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (5- ( ethylsulfonamido ) -6-fluoropyridin-2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.67 (s, 1H), 8.39 (s, 1H), 8.01 (d, J = 9.7 Hz, 1H), 7.92 (d, J = 8.3 Hz, 1H), 7.47 (t, J = 3.0 Hz, 1H), 6.89 (dd, J = 1.9, 3.5 Hz, 1H), 3.20 (d, J = 7.4 Hz, 2H), 2.10-1.97 ( m, 1H), 1.28-1.22 (m, 3H), 0.87-0.76 (m, 4H)

MS (ESI +) m / z 404 (M + H) ⁺

Example  150: N- (4- (6- Fluoro -5- ( Propylsulfonamido Pyridin-2-yl) -1 H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (6-fluoro-5- (propylsulfonamido) pyridin-2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.62 (s, 1H), 10.68 (s, 1H), 10.14 (s, 1H), 8.40 (s, 1H), 8.12-8.01 (m, 1H), 7.94 (d, J = 8.1 Hz, 1H), 7.48 (dd, J = 2.6, 3.5 Hz, 1H), 6.89 (dd, J = 1.9, 3.5 Hz, 1H), 3.26-3.16 (m, 2H), 2.04 (t, J = 3.9 Hz, 1H), 1.76 (h, J = 7.5 Hz, 2H), 0.99 (t, J = 7.4 Hz, 3H), 0.89-0.78 (m, 4H)

MS (ESI +) m / z 418 (M + H) ⁺

Example  151: N- (4- (4- ( Ethylsulfonamido ) Cyclohex -1-en-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (ethylsulfonamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.39 (s, 1H), 10.52 (s, 1H), 7.83 (s, 1H), 7.31 (t, J = 3.0 Hz, 1H), 7.22 (d, J = 7.3 Hz, 1H), 6.50 (d, J = 3.4 Hz, 1H), 6.18 (s, 1H), 3.06 (q, J = 7.3 Hz, 2H), 2.24 (d, J = 9.8 Hz, 1H) , 2.01 (s, 2H), 1.76-1.61 (m, 1H), 1.21 (d, J = 7.4 Hz, 3H), 0.82-0.74 (m, 4H)

MS (ESI +) m / z 389 (M + H) ⁺

Example  152: N- (4- (4- ( Propyl sulfonamide ) Cyclohex -1-en-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropane Carboxamide  Synthesis of (N- (4- (4- (propylsulfonamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.39 (s, 1H), 10.52 (s, 1H), 7.83 (s, 1H), 7.31 (t, J = 2.9 Hz, 1H), 7.21 (d, J = 7.4 Hz, 1H), 6.51 (dd, J = 1.8, 3.5 Hz, 1H), 6.18 (s, 1H), 3.11-2.99 (m, 2H), 2.22 (dd, J = 9.0, 17.2 Hz, 1H) , 2.01 (s, 2H), 1.76-1.63 (m, 3H), 0.99 (t, J = 7.4 Hz, 3H), 0.81-0.72 (m, 4H)

MS (ESI +) m / z 403 (M + H) ⁺

Example  153: N- (4- (4-(( Trifluoromethyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((trifluoromethyl) sulfonamido) cyclohex-1 -en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.56 (s, 1H), 9.62 (d, J = 7.9 Hz, 1H), 7.82 (s, 1H), 7.32 (t, J = 3.0 Hz, 1H), 6.53 (dd, J = 1.8, 3.5 Hz, 1H), 6.18 (s, 1H), 3.71 (s, 2H), 2.70-2.55 (m, 5H), 2.34 (d, J = 8.2 Hz, 1H), 2.02 (s, 2H), 1.82 (s, 1H), 0.84-0.76 (m, 4H)

MS (ESI +) m / z 429 (M + H) ⁺

Example  154: N- (4- (4- ( Cyclopropanesulfonamido ) Cyclohex -1-en-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (cyclopropanesulfonamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, Chloroform-d) δ 11.37 (s, 1H), 10.49 (s, 1H), 7.83 (s, 1H), 7.31 (dd, J = 2.4, 3.5 Hz, 1H), 7.22 (d , J = 7.5 Hz, 1H), 6.51 (dd, J = 1.9, 3.5 Hz, 1H), 6.19 (s, 1H), 3.54 (d, J = 3.3 Hz, 1H), 2.68-2.55 (m, 4H) , 2.30-2.19 (m, 1H), 2.08 (d, J = 13.3 Hz, 1H), 2.00 (dt, J = 4.8, 8.4 Hz, 1H), 1.72 (ddt, J = 5.7, 10.1, 15.5 Hz, 1H ), 0.98-0.93 (m, 4H), 0.84-0.75 (m, 4H)

MS (ESI +) m / z 401 (M + H) ⁺

Example  155: N- (4- (4-((2- Cyanoethyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((2-cyanoethyl) sulfonamido) cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.49 (s, 1H), 7.83 (s, 1H), 7.33-7.27 (m, 1H), 6.50 (dd, J = 1.4 , 3.5 Hz, 1H), 6.18 (t, J = 3.4 Hz, 1H), 3.49 (q, J = 9.4, 10.2 Hz, 2H), 3.20-3.14 (m, 2H), 2.68 (t, J = 7.2 Hz , 2H), 2.58 (d, J = 18.9 Hz, 3H), 2.28-2.17 (m, 1H), 2.06-1.96 (m, 4H), 1.77-1.64 (m, 1H), 0.85-0.76 (m, 4H )

MS (ESI +) m / z 414 (M + H) ⁺

Example  156: N- (4- (4-(((1- ( Cyanomethyl ) Cyclopropyl ) methyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1- (cyanomethyl) cyclopropyl) ) methyl) sulfonamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.49 (s, 1H), 7.83 (s, 1H), 7.39 (d, J = 6.9 Hz, 1H), 7.31 (dd, J = 2.5, 3.5 Hz, 1H), 6.50 (dd, J = 1.9, 3.5 Hz, 1H), 6.18 (s, 1H), 3.51 (s, 1H), 3.18 (s, 2H), 2.83 (s, 2H ), 2.58 (d, J = 22.9 Hz, 3H), 2.23 (dd, J = 12.2, 23.6 Hz, 1H), 2.01 (s, 2H), 1.78-1.63 (m, 1H), 0.84-0.79 (m, 4H), 0.79-0.73 (m, 2H), 0.71- 0.65 (m, 2H)

MS (ESI +) m / z 454 (M + H) ⁺

Example  157: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl) methyl) sulfonamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.49 (s, 1H), 7.83 (s, 1H), 7.51 (s, 1H), 7.31 (dd, J = 2.5, 3.5 Hz, 1H), 6.50 (dd, J = 1.9, 3.5 Hz, 1H), 6.18 (s, 1H), 3.52 (d, J = 16.4 Hz, 1H), 3.37 (s, 2H), 2.59 (d, J = 29.8 Hz, 3H), 2.24 (dd, J = 9.4, 16.1 Hz, 1H), 2.12-1.97 (m, 2H), 1.78-1.63 (m, 1H), 1.36 (t, J = 3.5 Hz, 2H) , 1.29-1.23 (m, 2H), 0.86-0.74 (m, 4H)

MS (ESI +) m / z 440 (M + H) ⁺

Example  158: N- (4- (4-((3- Cyanopropyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3-cyanopropyl) sulfonamido) cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.49 (s, 1H), 7.83 (s, 1H), 7.40 (d, J = 6.4 Hz, 1H), 7.31 (dd, J = 2.4, 3.5 Hz, 1H), 6.50 (dd, J = 1.8, 3.5 Hz, 1H), 6.18 (s, 1H), 3.49 (s, 2H), 3.17 (dd, J = 6.4, 8.7 Hz, 2H ), 2.68 (t, J = 7.3 Hz, 2H), 2.58 (d, J = 18.3 Hz, 3H), 2.23 (dd, J = 8.9, 17.2 Hz, 1H), 2.00 (h, J = 6.2, 7.3 Hz , 4H), 1.76-1.63 (m, 1H), 0.83-0.75 (m, 4H)

MS (ESI +) m / z 428 (M + H) ⁺

Example  159: N- (4- (4-((3- Fluoropropyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3-fluoropropyl) sulfonamido) cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.39 (s, 1H), 10.52 (s, 1H), 7.83 (s, 1H), 7.36 (d, J = 7.3 Hz, 1H), 7.31 (dd, J = 2.5, 3.5 Hz, 1H), 6.51 (dd, J = 1.9, 3.5 Hz, 1H), 6.18 (d, J = 4.3 Hz, 1H), 4.62 (t, J = 6.0 Hz, 1H), 4.51 ( t, J = 6.0 Hz, 1H), 3.50 (s, 1H), 3.24-3.11 (m, 2H), 2.55 (s, 3H), 2.23 (dd, J = 8.8, 15.7 Hz, 1H), 2.13-1.98 (m, 4H), 1.71 (tt, J = 8.0, 15.8 Hz, 1H), 0.83-0.74 (m, 4H)

MS (ESI +) m / z 421 (M + H) ⁺

Example  160: N- (4- (4- ( Allylsulfon Amido ) Cyclohex -1-en-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (allylsulfonamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.39 (s, 1H), 10.52 (s, 1H), 7.83 (d, J = 3.0 Hz, 1H), 7.34-7.26 (m, 2H), 6.50 ( dt, J = 1.6, 3.2 Hz, 1H), 6.17 (s, 1H), 5.45-5.36 (m, 1H), 3.87 (d, J = 7.2 Hz, 1H), 2.57 (d, J = 23.0 Hz, 2H ), 2.23 (d, J = 7.5 Hz, 1H), 2.01 (s, 2H), 1.87 (dd, J = 1.5, 6.7 Hz, 1H), 1.77-1.60 (m, 1H), 0.83-0.75 (m, 4H)

MS (ESI +) m / z 401 (M + H) ⁺

Example  161: N- (4- (4-(( Cyclopropylmethyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((cyclopropylmethyl) sulfonamido) cyclohex-1 -en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.39 (s, 1H), 10.52 (s, 1H), 7.83 (s, 1H), 7.31 (dd, J = 2.3, 3.5 Hz, 1H), 7.21 ( d, J = 6.1 Hz, 1H), 6.50 (dd, J = 1.6, 3.5 Hz, 1H), 6.18 (s, 1H), 3.51 (s, 1H), 3.01 (d, J = 6.9 Hz, 2H), 2.58 (d, J = 20.5 Hz, 3H), 2.23 (dd, J = 9.2, 16.8 Hz, 1H), 2.02 (s, 2H), 1.79-1.63 (m, 1H), 1.12-0.98 (m, 1H) , 0.84-0.74 (m, 4H)

MS (ESI +) m / z 415 (M + H) ⁺

Example  162: N- (4- (4-((3,4- Difluorophenyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3,4-difluorophenyl) sulfonamido ) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.51 (s, 1H), 7.92 (ddd, J = 2.2, 7.4, 9.8 Hz, 1H), 7.80 (s, 1H), 7.78-7.61 (m, 2H), 7.29 (dd, J = 2.2, 3.5 Hz, 1H), 6.47 (dd, J = 1.5, 3.5 Hz, 1H), 6.15-6.07 (m, 1H), 3.42-3.36 ( m, 2H), 2.40-2.28 (m, 1H), 2.12 (ddd, J = 3.1, 8.3, 18.0 Hz, 1H), 2.00 (tt, J = 4.9, 7.8 Hz, 1H), 1.85-1.77 (m, 1H), 1.68-1.53 (m, 1H), 0.82-0.73 (m, 4H)

MS (ESI +) m / z 473 (M + H) ⁺

Example  163: N- (4- (4-((3- Fluorophenyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3-fluorophenyl) sulfonamido) cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.50 (s, 1H), 7.79 (s, 1H), 7.75-7.63 (m, 3H), 7.56-7.48 (m, 1H ), 7.29 (dd, J = 2.2, 3.5 Hz, 1H), 6.47 (dd, J = 1.5, 3.5 Hz, 1H), 6.09 (d, J = 4.1 Hz, 1H), 2.49 (s, 3H), 2.39 -2.25 (m, 1H), 2.12 (ddd, J = 3.0, 8.5, 18.1 Hz, 1H), 1.99 (dt, J = 4.9, 7.5 Hz, 1H), 1.83-1.73 (m, 1H), 1.69-1.54 (m, 1H), 0.77 (tdd, J = 4.0, 6.4, 9.9 Hz, 4H)

MS (ESI +) m / z 455 (M + H) ⁺

Example  164: N- (4- (4-((4- Cyanophenyl ) Sulfonamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((4-cyanophenyl) sulfonamido) cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.51 (s, 1H), 8.21-8.15 (m, 1H), 8.13-8.07 (m, 2H), 8.07-8.01 (m , 2H), 7.79 (s, 1H), 7.29 (dd, J = 2.5, 3.5 Hz, 1H), 6.47 (dd, J = 1.9, 3.5 Hz, 1H), 6.09 (t, J = 3.7 Hz, 1H) , 3.40 (s, 2H), 3.17 (d, J = 3.2 Hz, 1H), 2.36-2.29 (m, 1H), 2.16-2.05 (m, 1H), 2.04-1.95 (m, 1H), 1.80 (d , J = 12.2 Hz, 1H), 1.63 (td, J = 5.8, 10.8, 11.7 Hz, 1H), 0.80-0.73 (m, 4H)

MS (ESI +) m / z 462 (M + H) ⁺

Example  165: N- (4- (4- ( Cyclobutanesulfone Amido ) Cyclohex -1-en-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (cyclobutanesulfonamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.51 (s, 1H), 7.82 (s, 1H), 7.31 (dd, J = 2.5, 3.5 Hz, 1H), 7.18 ( d, J = 7.7 Hz, 1H), 6.50 (dd, J = 1.8, 3.5 Hz, 1H), 6.17 (s, 1H), 3.94 (p, J = 8.2 Hz, 1H), 3.65-3.54 (m, 1H ), 2.37-2.14 (m, 5H), 2.06-1.80 (m, 4H), 1.69 (dd, J = 6.2, 11.5 Hz, 1H), 0.85-0.75 (m, 4H)

MS (ESI +) m / z 415 (M + H) ⁺

Example  166: N- (4- (1- ( Ethylsulfonyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (ethylsulfonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin- Synthesis of 6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 7.87 (s, 1H), 7.35 (t, J = 2.9 Hz, 1H), 6.57 (dd, J = 1.7, 3.6 Hz, 1H), 6.35 (d, J = 3.8 Hz, 1H), 4.00 (q, J = 2.9 Hz, 2H), 3.49 (t, J = 5.7 Hz, 4H), 3.14 (q, J = 7.3 Hz, 2H), 2.62 (s, 2H), 2.07-1.95 (m, 1H), 1.24 (t, J = 7.3 Hz, 3H), 0.84-0.77 (m, 4H)

MS (ESI +) m / z 375 (M + H) ⁺

Example  167: N- (4- (1-((3- Fluoropropyl ) Sulfonyl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-((3-fluoropropyl) sulfonyl) -1,2, Synthesis of 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 407 (M + H) ⁺

Example  168: N- (4- (1- ( Cyclopropylsulfonyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (cyclopropylsulfonyl) -1,2,3,6-tetrahydropyridin Synthesis of -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 387 (M + H) ⁺

Example  169: N- (4- (1-((( Tetrahydro -2H-pyran-4-yl) methyl ) Sulfonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-(((tetrahydro-2H-pyran-4-yl) methyl) sulfonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6- yl) cyclopropanecarboxamide)

MS (ESI +) m / z 445 (M + H) ⁺

Example  170: N- (4- (1-((3-cyanopropyl) sulfonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] Pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-((3-cyanopropyl) sulfonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2, Synthesis of 3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 414 (M + H) ⁺

Example  171: N- (4- (1-(((1- ( Cyanomethyl ) Cyclopropyl ) methyl ) Sulfonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-(((1- (cyanomethyl) cyclopropyl) methyl) sulfonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

MS (ESI +) m / z 440 (M + H) ⁺

Example  172: N- (4- (1-(((1- Cyanocyclopropyl ) methyl ) Sulfonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-(((1-cyanocyclopropyl) methyl) sulfonyl) -1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 426 (M + H) ⁺

Example  173: N- (4- (1-((3,4- Difluorophenyl ) Sulfonyl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-((3,4-difluorophenyl) sulfonyl) -1, 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 459 (M + H) ⁺

Example  174: N- (4- (8- ( Ethylsulfonyl )-8- Azabicyclo [3.2.1] oct -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (ethylsulfonyl) -8-azabicyclo [3.2 .1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 401 (M + H) ⁺

Example  175: N- (4- (8-((3- Fluoropropyl ) Sulfonyl) -8- Azabicyclo [3.2.1] oct -2-en-3-yl) -1H-pyrrolo [2,3-b] cyclopropane Carboxamide  (N- (4- (8-((3-fluoropropyl) sulfonyl) -8-azabicyclo [3.2.1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

MS (ESI +) m / z 433 (M + H) ⁺

Example  176: N- (4- (8- ( Propylsulfonyl )-8- Azabicyclo [3.2.1] oct -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (propylsulfonyl) -8-azabicyclo [3.2 .1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 415 (M + H) ⁺

Example  177: N- (4- (8- ( Cyclopropylsulfonyl )-8- Azabicyclo [3.2.1] oct -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (cyclopropylsulfonyl) -8-azabicyclo [3.2 .1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 413 (M + H) ⁺

Example  178: N- (4- (8-((3,4- Difluorophenyl ) Sulfonyl) -8- Azabicyclo [3.2.1] oct 2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8-((3,4-difluorophenyl) sulfonyl ) -8-azabicyclo [3.2.1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 485 (M + H) ⁺

Example  179: N- (4- (1- ( Ethylsulfonyl ) -3,3-dimethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (ethylsulfonyl) -3,3-dimethyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.53 (s, 1H), 7.74 (s, 1H), 7.28 (dd, J = 2.4, 3.5 Hz, 1H), 6.28 ( dd, J = 1.9, 3.5 Hz, 1H), 5.62 (t, J = 3.2 Hz, 1H), 3.89 (d, J = 3.2 Hz, 2H), 3.19 (s, 2H), 3.15 (t, J = 7.3 Hz, 2H), 2.01 (s, 1H), 1.27 (t, J = 7.4 Hz, 3H), 1.04 (s, 6H), 0.82-0.75 (m, 4H)

MS (ESI +) m / z 403 (M + H) ⁺

Example  180: N- (4- (1-((3- Cyanopropyl ) Sulfonyl) -3,3-dimethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-((3-cyanopropyl) sulfonyl) -3,3- Synthesis of dimethyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.54 (s, 1H), 7.74 (s, 1H), 7.29 (dd, J = 2.4, 3.5 Hz, 1H), 6.28 ( dd, J = 1.9, 3.5 Hz, 1H), 5.62 (t, J = 3.2 Hz, 1H), 3.90 (d, J = 3.2 Hz, 2H), 3.28-3.18 (m, 4H), 2.68 (t, J = 7.2 Hz, 2H), 2.03 (q, J = 7.5 Hz, 3H), 1.05 (s, 6H), 0.82-0.76 (m, 4H)

MS (ESI +) m / z 442 (M + H) ⁺

Example  181: N- (4- (4-((3,4- Difluorophenyl ) Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((3,4-difluorophenyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide) Synthesis of

MS (ESI +) m / z 470 (M + H) ⁺

Example  182: N- (4- (4- ( Ethylsulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 386 (M + H) ⁺

Example  183: N- (4- (4- ( Cyclohexanesulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- ( cyclohexanesulfonamido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 440 (M + H) ⁺

Example  184: N- (4- (4-((4,4,4- Trifluorobutyl ) Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((4,4,4-trifluorobutyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) Synthesis of cyclopropanecarboxamide)

MS (ESI +) m / z 468 (M + H) ⁺

Example  185: N- (4- (4-((3-fluoropropyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropane carboxamide (N Synthesis of-(4- (4-((3-fluoropropyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 418 (M + H) ⁺

Example  186: N- (4- (4-((3- Cyanopropyl ) Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine Synthesis of -2-yl) cyclopropanecarboxamide (N- (4- (4-((3-cyanopropyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 425 (M + H) ⁺

Example  187: N- (4- (4-((4- Chlorophenyl ) Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine Synthesis of 2-yl) cyclopropanecarboxamide (N- (4- (4-((4-chlorophenyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 468, 470 (M + H) ⁺

Example  188: N- (4- (4-((4- Fluorophenyl ) Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine Synthesis of 2-yl) cyclopropanecarboxamide (N- (4- (4-((4-fluorophenyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 452 (M + H) ⁺

Example  189: N- (4- (4-((4- Bromophenyl ) Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine Synthesis of 2-yl) cyclopropanecarboxamide (N- (4- (4-((4-bromophenyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 512, 514 (M + H) ⁺

Example  190: N- (4- (4- ( Propylsulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- ( propylsulfonamido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 400 (M + H) ⁺

Example  191: N- (4- (4- ( Butyl sulfon amido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- ( butylsulfonamido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 414 (M + H) ⁺

Example  192: N- (4- (4-((3- Fluorophenyl ) Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine Synthesis of-2-yl) cyclopropanecarboxamide (N- (4- (4-((3-fluorophenyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 452 (M + H) ⁺

Example  193: N- (4- (4- (3,4- Difluoro -N- Methylphenylsulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((3,4-difluoro-N-methylphenyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2- yl) cyclopropanecarboxamide)

MS (ESI +) m / z 484 (M + H) ⁺

Example  194: N- (4- (4-((3,3,3- Trifluoropropyl ) Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((3,3,3-trifluoropropyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) Synthesis of cyclopropanecarboxamide)

MS (ESI +) m / z 454 (M + H) ⁺

Example  195: N- (4- (4-((1,1- Dioxydotetrahydro -2H- Thiopyran )-4- Sulfonamido ) Phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide (N- (4- (4-((1,1-dioxidotetrahydro-2H-thiopyran) -4 -sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 490 (M + H) ⁺

Example  196: N- (4- (4-((1,1- Dioxydotetrahydrothiophene ) -3- Sulfonamido ) Phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide (N- (4- (4-((1,1-dioxidotetrahydrothiophene) -3-sulfonamido) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 476 (M + H) ⁺

Example  197: N- (4- (4-((6- Cyanopyridine ) -3- Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((6-cyanopyridine) -3-sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide ) Synthesis

MS (ESI +) m / z 460 (M + H) ⁺

Example  198: N- (4- (4-((1- methyl -1H-imidazole) -5- Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine -2 days) Cyclopropanecarboxamide  Synthesis of (N- (4- (4-((1-methyl-1H-imidazole) -5-sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 438 (M + H) ⁺

Example  199: N- (4- (4-((1- methyl -1H- Pyrazole )-4- Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((1-methyl-1H-pyrazole) -4-sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2 -yl) cyclopropanecarboxamide)

MS (ESI +) m / z 438 (M + H) ⁺

Example 200: 4 -(N- (4- (2- ( Cyclopropanecarboxamido ) -7H- Pyrrolo [2,3-d] pyrimidine -4-yl) phenyl) sulfamoyl) benzamide (4- (N- (4- (2- ( cyclopropanecarboxamido ) -7H-pyrrolo [2,3-d] pyrimidin-4-yl) phenyl) sulfamoyl) benzamide)

MS (ESI +) m / z 477 (M + H) ⁺

Example  201: N- (4- (3- Fluoro -4-( Methylsulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine Synthesis of 2-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4- (methylsulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 12.10 (s, 1H), 10.62 (s, 1H), 8.06 (d, J = 9.4 Hz, 2H), 7.62 (t, J = 8.4 Hz, 1H) , 7.52 (s, 1H), 6.88 (s, 1H), 3.13 (s, 3H), 2.17 (s, 1H), 0.82 (d, J = 17.7 Hz, 4H)

MS (ESI +) m / z 390 (M + H) ⁺

Example  202: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) -3-fluorophenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 12.10 (s, 1H), 10.62 (s, 1H), 9.94 (s, 1H), 8.15-7.99 (m, 2H), 7.63 (t, J = 8.3 Hz, 1H), 7.57-7.47 (m, 1H), 6.94-6.84 (m, 1H), 3.21 (q, J = 7.3 Hz, 2H), 2.17 (s, 1H), 1.28 (t, J = 7.1 Hz , 3H), 0.88-0.75 (m, 4H)

MS (ESI +) m / z 404 (M + H) ⁺

Example  203: N- (4- (3- Fluoro -4-((3- Fluoropropyl ) Sulfonamido ) Phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4-((3-fluoropropyl) sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 12.10 (s, 1H), 10.62 (s, 1H), 10.08 (s, 1H), 8.06 (d, J = 9.9 Hz, 2H), 7.63 (t, J = 8.2 Hz, 1H), 7.56-7.48 (m, 1H), 6.95-6.85 (m, 1H), 4.55 (dt, J = 6.0, 47.4 Hz, 2H), 2.14 (dd, J = 8.0, 22.9 Hz , 3H), 0.84-0.78 (m, 4H)

MS (ESI +) m / z 436 (M + H) ⁺

Example  204: N- (4- (4-((3- Cyanopropyl ) Sulfonamido ) -3- Fluorophenyl ) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((3-cyanopropyl) sulfonamido) -3-fluorophenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 12.10 (s, 1H), 10.63 (s, 1H), 10.12 (s, 1H), 8.06 (d, J = 10.0 Hz, 2H), 7.62 (t, J = 8.3 Hz, 1H), 7.58-7.46 (m, 1H), 6.95-6.78 (m, 1H), 2.69 (t, J = 7.1 Hz, 2H), 2.17 (s, 1H), 2.07 (q, J = 7.3 Hz, 2H), 0.88-0.80 (m, 4H)

MS (ESI +) m / z 443 (M + H) ⁺

Example  205: N- (4- (4-((3,4- Difluorophenyl ) Sulfonamido ) -3- Fluorophenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide (N- (4- (4-((3,4-difluorophenyl) sulfonamido) -3-fluorophenyl)- Synthesis of 7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 12.11 (s, 1H), 10.67 (s, 1H), 10.62 (s, 1H), 8.06-7.93 (m, 2H), 7.91-7.83 (m, 1H ), 7.76-7.61 (m, 2H), 7.57-7.44 (m, 2H), 6.91-6.78 (m, 1H), 2.14 (s, 1H), 0.90-0.74 (m, 4H)

MS (ESI +) m / z 488 (M + H) ⁺

Example  206: N- (4- (3-fluoro-4- (propylsulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropane Carboxamide  Synthesis of (N- (4- (3-fluoro-4- (propylsulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 418 (M + H) ⁺

Example  207: N- (7- (4- ( Ethylsulfonamido ) Phenyl) -3H- Imidazo [4,5-b] pyridine -5-yl) cyclopropanecarboxamide (N- (7- (4- ( ethylsulfonamido ) phenyl ) -3H-imidazo [4,5-b] pyridin-5-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 386 (M + H) ⁺

Example  208: N- (6- (4-((3,4- Difluorophenyl ) Sulfonamido ) Phenyl) -9H- Purin 2-yl) cyclopropanecarboxamide (N- (6- (4-((3,4- difluorophenyl ) sulfonamido ) phenyl ) -9H-purin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.80 (s, 1H), 10.72 (s, 1H), 8.81-8.61 (m, 2H), 8.45 (s, 1H), 7.92 (ddd, J = 9.7 , 7.3, 2.2 Hz, 1H), 7.76-7.59 (m, 2H), 7.36-7.28 (m, 2H), 2.16 (s, 1H), 0.85-0.77 (m, 4H)

MS (ESI +) m / z 471 (M + H) ⁺

Example  209: N- (6- (4- ( Ethylsulfonamido ) Phenyl) -9H- Purin -2 days) Cyclopropanecarboxamide  (N- (6- (4- ( ethylsulfonamido ) phenyl ) -9H- purin -2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.73 (s, 1H), 10.18 (s, 1H), 8.77 (d, J = 8.4 Hz, 2H), 8.46 (d, J = 1.3 Hz, 1H) , 7.46-7.34 (m, 2H), 3.26-3.18 (m, 2H), 2.26-2.13 (m, 1H), 1.22 (td, J = 7.4, 1.3 Hz, 3H), 0.92-0.80 (m, 4H)

MS (ESI +) m / z 387 (M + H) ⁺

Example  210: N- (6- (4-((3- Cyanopropyl ) Sulfonamido ) Phenyl) -9H- Purin -2 days) Cyclopropanecarboxamide  (N- (6- (4-((3- cyanopropyl ) sulfonamido ) phenyl ) -9H- purin -2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.77 (s, 1H), 10.32 (s, 1H), 8.83-8.75 (m, 2H), 8.48 (s, 1H), 7.45-7.36 (m, 2H ), 3.59 (dq, J = 12.1, 6.0 Hz, 2H), 3.35-3.25 (m, 2H), 2.19 (dt, J = 7.8, 3.3 Hz, 1H), 2.00 (dq, J = 9.5, 7.4 Hz, 2H), 1.03 (d, J = 6.1 Hz, 6H), 0.91-0.79 (m, 4H)

MS (ESI +) m / z 426 (M + H) ⁺

Example  211: N- (6- (4-((4,4,4- Trifluorobutyl ) Sulfonamido ) Phenyl) -9H- Purin Synthesis of 2-yl) cyclopropanecarboxamide (N- (6- (4-((4,4,4-trifluorobutyl) sulfonamido) phenyl) -9H-purin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.74 (s, 1H), 10.31 (s, 1H), 8.78 (d, J = 8.7 Hz, 2H), 8.47 (s, 1H), 7.43-7.35 ( m, 2H), 3.34 (t, J = 7.6 Hz, 2H), 2.49-2.34 (m, 2H), 2.19 (td, J = 7.3, 3.7 Hz, 1H), 1.97-1.84 (m, 2H), 0.86 0.78 (m, 4H)

MS (ESI +) m / z 469 (M + H) ⁺

Example  212: N- (4- (1- ( Propylsulfonyl ) -2,5- Dehydro -1H-pyrrole-3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (propylsulfonyl) -2,5-dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] pyridin- Synthesis of 6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.57 (s, 1H), 10.61 (s, 1H), 7.82 (s, 1H), 7.43 (t, J = 2.9 Hz, 1H), 6.70 (td, J = 1.9, 3.6, 4.2 Hz, 2H), 4.58 (t, J = 4.4 Hz, 2H), 4.40 (q, J = 3.8 Hz, 2H), 3.26-3.15 (m, 2H), 2.03 (tt, J = 4.5, 7.7 Hz, 1H), 1.80-1.65 (m, 2H), 1.00 (t, J = 7.4 Hz, 3H), 0.83-0.76 (m, 4H)

MS (ESI +) m / z 375 (M + H) ⁺

Example  213: N- (4- (1-(((1- Cyanocyclopropyl ) methyl ) Sulfonyl) -2,5- Dehydro -1H-pyrrole-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-(((1-cyanocyclopropyl) methyl) sulfonyl) -2,5-dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.58 (s, 1H), 10.62 (s, 1H), 7.83 (s, 1H), 7.52-7.35 (m, 1H), 6.75-6.65 (m, 2H ), 4.64 (dd, J = 3.1, 6.2 Hz, 2H), 4.46 (q, J = 3.2, 3.7 Hz, 2H), 3.61 (s, 2H), 2.02 (td, J = 4.0, 7.6 Hz, 1H) , 1.40 (q, J = 4.3, 4.7 Hz, 2H), 1.22 (q, J = 4.9 Hz, 2H), 0.89-0.73 (m, 4H)

MS (ESI +) m / z 412 (M + H) ⁺

Example  214: N- (4- (4- (morpholine-4- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( morpholine -4- sulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

Starting material N- (4- (4-aminophenyl) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-aminophenyl ) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) (100 mg) was stirred in 1 mL of pyridine. 1.5 equivalents of morpholine-4-sulfonylchloride were added and stirred at 40 ^° C. for 16 hours. After the reaction was completed, the mixture was added with d-HCl, extracted with dichloromethane, and the organic layer was separated. After concentration of the mixture, it was dissolved in a MeOH / THF (1: 1) solution, 2N aqueous sodium hydroxide solution was added, and stirred at 30 ^° C. for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature and saturated NH ₄ Cl aqueous solution was added with stirring. The resulting solid was filtered to give the product N- (4- (4- (morpholin-4-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarbox Mid was obtained.

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.69 (s, 1H), 10.24 (s, 1H), 7.97 (d, J = 5.7 Hz, 1H), 7.69 (d, J = 7.6 Hz, 2H), 7.47 (d, J = 8.2 Hz, 1H), 7.43-7.33 (m, 3H), 7.11 (d, J = 7.8 Hz, 1H), 6.62-6.51 (m, 1H), 3.63-3.50 (m, 5H), 3.18-3.06 (m, 5H), 2.05 (d, J = 8.9 Hz, 1H), 0.88-0.77 (m, 4H)

MS (ESI +) m / z 442 (M + H) ⁺

Examples 215-238

In Examples 215 to 238, the synthesis was carried out in the same manner as in Example 214, or by using a suitable reactant in consideration of the scheme 1 and the structure of the compound to be prepared.

Example  215: N- (4- (4-((N-ethyl-N-) Methylsulfamoyl ) Amino) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((N-ethyl-N-methylsulfamoyl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.59 (s, 1H), 10.07 (s, 1H), 7.99 (s, 1H), 7.71-7.60 (m, 2H), 7.43-7.35 (m, 1H), 7.31 (d, J = 8.5 Hz, 2H), 6.58-6.48 (m, 1H), 3.18 (q, J = 7.2 Hz, 2H), 2.74 (s, 3H), 2.04 (s, 1H), 1.04 (t, J = 7.0 Hz, 3H), 0.88-0.74 (m, 4H)

MS (ESI +) m / z 414 (M + H) ⁺

Example  216: N- (4- (4-(( N, N - Diethylsulfamoyl ) Amino) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((N, N-diethylsulfamoyl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.59 (s, 1H), 10.02 (s, 1H), 7.99 (s, 1H), 7.65 (d, J = 8.0 Hz, 2H), 7.44-7.19 (m, 3H), 6.54 (d, J = 10.6 Hz, 1H), 3.23 (t, J = 6.9 Hz, 4H), 2.04 (s, 1H), 1.01 (t, J = 7.2 Hz, 6H), 0.88-0.76 (m, 4H)

MS (ESI +) m / z 428 (M + H) ⁺

Example  217: N- (4- (4-((N- Cyclopropyl -N- Methylsulfamoyl ) Amino) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((N-cyclopropyl-N-methylsulfamoyl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.59 (s, 1H), 10.26 (s, 1H), 7.98 (s, 1H), 7.65 (d, J = 8.1 Hz, 2H), 7.45-7.26 (m, 3H), 6.54 (s, 1H), 2.80 (t, J = 5.5 Hz, 3H), 2.34 (s, 1H), 2.04 (s, 1H), 0.88-0.76 (m , 4H), 0.63 (d, J = 22.6 Hz, 4H)

MS (ESI +) m / z 426 (M + H) ⁺

Example  218: N- (4- (4- ( Pyrrolidine -One- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( pyrrolidine -One- sulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 426 (M + H) ⁺

Example  219: N- (4- (4- (piperidine-1- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( piperidine -One- sulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 440 (M + H) ⁺

Example  220: N- (4- (4-((2,6-dimethylmorpholine) -4- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((2,6-dimethylmorpholine) -4-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

MS (ESI +) m / z 470 (M + H) ⁺

Example  221: N- (4- (4-((3- Cyanoazetidine )-One- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((3- cyanoazetidine ) -1-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 437 (M + H) ⁺

Example  222: N- (4- (4-((N-isopropyl-N-) Methylsulfamoyl ) Amino) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((N-isopropyl-N-methylsulfamoyl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.58 (s, 1H), 10.06 (s, 1H), 7.98 (s, 1H), 7.65 (d, J = 7.9 Hz, 2H), 7.38 (s, 1H), 7.26 (d, J = 9.5 Hz, 2H), 6.52 (s, 1H), 4.03 (s, 1H), 2.65 (t, J = 5.8 Hz, 3H), 2.04 ( s, 1H), 1.03-0.95 (m, 6H), 0.81 (s, 4H)

MS (ESI +) m / z 428 (M + H) ⁺

Example  223: N- (4- (4-((N- (2- Methoxyethyl ) -N- Methylsulfamoyl ) Amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((N- (2-methoxyethyl) -N-methylsulfamoyl ) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.59 (s, 1H), 10.07 (s, 1H), 7.99 (s, 1H), 7.66 (d, J = 9.1 Hz, 2H), 7.35 (t, J = 14.4 Hz, 3H), 6.53 (s, 1H), 3.41 (s, 2H), 3.19 (q, J = 5.6, 6.3 Hz, 3H), 2.81 (t, J = 5.9 Hz, 3H), 2.04 (s, 1H), 0.90-0.73 (m, 4H)

MS (ESI +) m / z 444 (M + H) ⁺

Example  224: N- (4- (3- Fluoro -4- (piperidine-1- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4- (piperidine-1-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.68 (s, 1H), 9.85 (s, 1H), 8.02 (s, 1H), 7.61 (t, J = 8.2 Hz, 1H), 7.54 (d, J = 9.9 Hz, 2H), 7.43 (t, J = 3.0 Hz, 1H), 6.58-6.54 (m, 1H), 3.12 (d, J = 6.2 Hz, 4H), 2.04 ( s, 1H), 1.47 (d, J = 20.7 Hz, 6H), 0.85-0.78 (m, 4H)

MS (ESI +) m / z 458 (M + H) ⁺

Example  225: N- (4- (3- Fluoro -4-( Pyrrolidine -One- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4- (pyrrolidine-1-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.67 (s, 1H), 9.81 (s, 1H), 8.01 (s, 1H), 7.62 (t, J = 8.3 Hz, 1H), 7.53 (d, J = 8.4 Hz, 2H), 7.43 (t, J = 3.0 Hz, 1H), 6.55 (dd, J = 3.6, 1.9 Hz, 1H), 3.21 (d, J = 6.0 Hz, 4H), 2.04 (s, 1H), 1.83-1.72 (m, 4H), 0.90-0.70 (m, 4H)

MS (ESI +) m / z 444 (M + H) ⁺

Example  226: N- (4- (3- Fluoro -4- (morpholine-4- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3- fluoro -4-( morpholine Synthesis of -4-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.69 (s, 1H), 10.02 (s, 1H), 8.03 (s, 1H), 7.63 (t, J = 8.4 Hz, 1H), 7.60-7.52 (m, 2H), 7.44 (t, J = 3.0 Hz, 1H), 6.56 (dd, J = 3.6, 1.9 Hz, 1H), 3.60 (t, J = 4.7 Hz, 4H), 3.10 (t, J = 4.7 Hz, 4H), 2.04 (s, 1H), 0.90-0.68 (m, 4H)

MS (ESI +) m / z 460 (M + H) ⁺

Example  227: N- (4- (2- methyl -4-((N- (2,2,2- Trifluoroethyl ) Sulfa Mole ) Amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (2-methyl-4-((N- (2,2, Synthesis of 2-trifluoroethyl) sulfamoyl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59-11.42 (m, 1H), 10.63 (s, 1H), 7.76 (s, 1H), 7.38-7.26 (m, 1H), 7.21 (d, J = 8.1 Hz, 1H), 7.15 (d, J = 2.2 Hz, 1H), 7.09 (dd, J = 2.4, 8.3 Hz, 1H), 6.07 (dd, J = 1.9, 3.5 Hz, 1H), 3.70 (q , J = 9.6 Hz, 2H), 2.14 (s, 3H), 2.04 (d, J = 7.2 Hz, 1H), 0.82-0.75 (m, 4H)

MS (ESI +) m / z 468 (M + H) ⁺

Example  228: N- (4- (2- methyl -4-((N- methyl -N- (2,2,2- Trifluoroethyl ) Sulfa Mole ) Amino) phenyl) -1H-pyrrolo [2,3-b] cyclopropane Carboxamide  (N- (4- (2-methyl-4-((N-methyl-N- (2,2,2-trifluoroethyl) sulfamoyl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (d, J = 6.3 Hz, 1H), 10.64 (s, 1H), 7.77 (s, 1H), 7.34 (d, J = 3.7 Hz, 1H) , 7.23 (d, J = 8.0 Hz, 1H), 7.17-7.07 (m, 2H), 6.09-6.04 (m, 1H), 4.06 (d, J = 10.1 Hz, 2H), 2.92-2.85 (m, 3H ), 2.14 (s, 3H), 2.04 (s, 1H), 0.82-0.75 (m, 4H)

MS (ESI +) m / z 482 (M + H) ⁺

Example  229: N- (4- (4-((1,1- Dioxidothiomorpholine )-4- Sulfonamido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1,1-dioxidothiomorpholine) -4-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (s, 1H), 10.39 (s, 1H), 8.01 (s, 1H), 7.71 (d, J = 8.3 Hz, 2H), 7.38 (t, J = 6.7 Hz, 3H), 6.58-6.50 (m, 1H), 3.66 (d, J = 5.5 Hz, 4H), 3.16 (d, J = 5.3 Hz, 4H), 2.04 ( s, 1H), 0.85-0.76 (m, 4H)

MS (ESI +) m / z 490 (M + H) ⁺

Example  230: N- (4- (4-((4- ( Methylsulfonyl Piperazine) -1- Sulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4- (methylsulfonyl) piperazine) -1-sulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6- yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.61 (s, 1H), 10.30 (s, 1H), 8.00 (s, 1H), 7.69 (d, J = 8.3 Hz, 2H), 7.42-7.34 (m, 3H), 6.54 (d, J = 2.9 Hz, 1H), 3.26 (t, J = 4.8 Hz, 4H), 3.13 (d, J = 5.5 Hz, 4H), 2.85 ( s, 3H), 2.04 (s, 1H), 0.85-0.77 (m, 4H)

MS (ESI +) m / z 519 (M + H) ⁺

Example  231: N- (4- (4- (morpholine-4- Sulfonamido ) Cyclohex -1-en-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (morpholine-4-sulfonamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.39 (s, 1H), 10.52 (s, 1H), 7.83 (d, J = 3.1 Hz, 1H), 7.31 (s, 1H), 6.51 (s, 1H), 6.19 (d, J = 4.1 Hz, 1H), 3.66 (d, J = 4.7 Hz, 4H), 3.06-2.99 (m, 4H), 2.58 (d, J = 22.0 Hz, 4H), 2.25 ( d, J = 14.2 Hz, 1H), 2.01 (d, J = 12.6 Hz, 2H), 1.70 (s, 1H), 0.84-0.76 (m, 4H)

MS (ESI +) m / z 446 (M + H) ⁺

Example  232: N- (4- (1- (N- (2,2,2- Trifluoroethyl ) Sulfa Mole ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (N- (2,2,2-trifluoroethyl) sulfamoyl ) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.55 (s, 1H), 8.10 (s, 1H), 7.87 (s, 1H), 7.41-7.29 (m, 1H), 6.57 (s, 1H), 6.36 (s, 1H), 3.89 (s, 2H), 3.79 (d, J = 10.4 Hz, 2H), 2.64 (s, 2H), 2.07-1.97 (m, 1H), 0.79 (d, J = 12.6 Hz, 4H)

MS (ESI +) m / z 444 (M + H) ⁺

Example  233: N- (4- (1- (N-methyl-N- (2,2,2-trifluoroethyl) sulfamoyl) -1,2,3,6-tetrahydropyridin-4-yl)- 1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (N-methyl-N- (2,2,2-trifluoroethyl) sulfamoyl)- 1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.55 (s, 1H), 7.87 (d, J = 3.8 Hz, 1H), 7.36 (s, 1H), 6.56 (s, 1H), 6.35 (s, 1H), 4.11 (d, J = 10.7 Hz, 2H), 3.96 (s, 2H), 3.48 (s, 4H), 2.93 (d, J = 3.8 Hz, 2H), 2.63 ( s, 2H), 2.02 (s, 1H), 0.79 (d, J = 12.0 Hz, 4H)

MS (ESI +) m / z 458 (M + H) ⁺

Example  234: N- (4- (1- ( Morpholinosulfonyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (morpholinosulfonyl) -1,2,3,6-tetrahydropyridin Synthesis of -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 432 (M + H) ⁺

Example  235: N- (4- (4- (morpholine-4- Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- ( morpholine -4- sulfonamido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 443 (M + H) ⁺

Example  236: N- (4- (4-(( N, N - Dimethyl sulfamoyl ) Amino) phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((N, N-dimethylsulfamoyl) amino) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide) Synthesis of

MS (ESI +) m / z 401 (M + H) ⁺

Example  237: N- (4- (4-((2,6-dimethylmorpholine) -4- Sulfonamido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((2,6-dimethylmorpholine) -4-sulfonamido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 12.01 (s, 1H), 10.56 (s, 1H), 10.30 (s, 1H), 8.19-8.13 (m, 2H), 7.51-7.45 (m, 2H ), 7.38 (dd, J = 2.1, 9.1 Hz, 2H), 6.84 (dd, J = 1.8, 3.7 Hz, 1H), 3.53-3.45 (m, 4H), 2.41 (d, J = 14.6 Hz, 2H) , 2.19 (d, J = 9.7 Hz, 1H), 1.06 (dd, J = 2.9, 6.4 Hz, 6H), 0.89-0.75 (m, 4H)

MS (ESI +) m / z 471 (M + H) ⁺

Example  238: N- (6- (4- (morpholine-4- Sulfonamido ) Phenyl) -9H- Purin -2 days) Cyclopropanecarboxamide  (N- (6- (4- ( morpholine -4- sulfonamido ) phenyl ) -9H- purin -2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.74 (s, 1H), 10.39 (s, 1H), 8.77 (d, J = 8.5 Hz, 2H), 8.47 (s, 1H), 7.39 (d, J = 8.4 Hz, 2H), 3.55 (t, J = 4.8 Hz, 4H), 3.13 (t, J = 4.7 Hz, 4H), 2.18 (dd, J = 8.7, 4.3 Hz, 1H), 0.90-0.77 ( m, 4H)

MS (ESI +) m / z 444 (M + H) ⁺

Example  239: N- (4- (4- (2-cyanoacetamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- Synthesis of (4- (2-cyanoacetamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

1.2 equivalents of 2-cyanoacetic acid were added to a dichloromethane solution and 1.6 equivalents of EDCI was added. To the mixture was added 1.4 equivalents of HOBt, 1.1 equivalents of DMAP, and synthesized N- (4- (4-aminophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (100 mg ) Was added and stirred at room temperature. After the reaction was completed, H ₂ O was added to the mixture, and extracted with dichloromethane to separate the organic layer. The mixture was concentrated, separated by column chromatography, and the product N- (4- (4- (2-cyanoacetamino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Cyclopropanecarboxamide was obtained.

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (s, 1H), 10.50 (s, 1H), 8.19 (d, J = 6.7 Hz, 2H), 8.02 (s, 1H), 7.40 (s, 1H), 6.89 (d, J = 6.8 Hz, 2H), 6.56 (s, 1H), 3.13 (s, 2H), 0.81 (d, J = 6.6 Hz, 4H)

MS (ESI +) m / z 360 (M + H) ⁺

Examples 240-430

Hereinafter, in Examples 240 to 430, synthesis was carried out in the same manner as in Example 239, or by using an appropriate reactant in consideration of the scheme 1 and the structure of the compound to be prepared.

Example  240: N- (4- (4- (2- Cyanoacetamido )-2- Methylphenyl ) -1H- Pyrrole [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- cyanoacetamido ) -2-methylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.62 (s, 1H), 10.41 (s, 1H), 7.78 (s, 1H), 7.54 (s, 1H), 7.49 ( d, J = 8.5 Hz, 1H), 7.33 (t, J = 2.9 Hz, 1H), 7.25 (d, J = 8.2 Hz, 1H), 6.07 (dd, J = 3.4, 1.8 Hz, 1H), 3.93 ( s, 2H), 2.15 (s, 3H), 2.03 (s, 1H), 0.84-0.75 (m, 4H)

MS (ESI +) m / z 374 (M + H) ⁺

Example  241: N- (4- (4- (2- (1- Cyanocyclopropyl ) Acetamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (1-cyanocyclopropyl) acetamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 10.19 (s, 1H), 8.10 (d, J = 6.2 Hz, 1H), 7.78 (d, J = 8.5 Hz, 2H), 7.69 (d, J = 8.4 Hz, 2H), 7.40 (t, J = 3.0 Hz, 1H), 6.56 (t, J = 2.5 Hz, 1H), 2.05 (s, 1H) , 1.28 (t, J = 3.8 Hz, 2H), 1.06 (q, J = 5.1 Hz, 2H), 0.88-0.79 (m, 4H)

MS (ESI +) m / z 400 (M + H) ⁺

Example  242: N- (4- (4- Propionamidocyclohex -1-en-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- propionamidocyclohex -One- en -1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.52 (s, 1H), 7.89-7.74 (m, 2H), 7.31 (dd, J = 2.5, 3.5 Hz, 1H), 6.51 (dd, J = 1.8, 3.5 Hz, 1H), 6.26-6.18 (m, 1H), 3.90 (s, 1H), 2.14 (d, J = 13.0 Hz, 1H), 2.08 (t, J = 7.6 Hz , 2H), 2.05-1.88 (m, 2H), 1.69-1.58 (m, 1H), 1.01 (t, J = 7.6 Hz, 3H), 0.84-0.76 (m, 4H)

MS (ESI +) m / z 353 (M + H) ⁺

Example  243: N- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) cyclohex-3-en-1-yl) benzamide (N- (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) cyclohex-3-en-1-yl) benzamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (s, 1H), 10.53 (s, 1H), 8.40 (d, J = 7.7 Hz, 1H), 7.88 (dt, J = 1.6, 7.1 Hz, 3H), 7.56-7.43 (m, 3H), 7.32 (dd, J = 2.4, 3.5 Hz, 1H), 6.54 (dd, J = 1.8, 3.6 Hz, 1H), 6.32-6.22 (m, 1H), 4.15 (d, J = 3.5 Hz, 1H), 2.71-2.54 (m, 4H), 2.41-2.29 (m, 1H), 2.04 (d, J = 13.0 Hz, 2H), 1.81 (tq, J = 5.6, 11.8 Hz, 1H), 0.85-0.74 (m, 4H)

MS (ESI +) m / z 401 (M + H) ⁺

Example  244: N- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) cyclohex-3-en-1-yl) -2-methylcyclopropane-1-carboxamide (N- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b ] Synthesis of pyridin-4-yl) cyclohex-3-en-1-yl) -2-methylcyclopropane-1-carboxamide)

MS (ESI +) m / z 379 (M + H) ⁺

Example  245: N- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) cyclohex-3-en-1-yl) cyclopentane Carboxamide  Synthesis of (N- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) cyclohex-3-en-1-yl) cyclopentanecarboxamide)

MS (ESI +) m / z 393 (M + H) ⁺

Example  246: N- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) cyclohex-3-en-1-yl) cyclopropanecarboxamide (N- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) Synthesis of cyclohex-3-en-1-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.51 (s, 1H), 8.13 (d, J = 7.5 Hz, 1H), 7.84 (s, 1H), 7.31 (d, J = 3.5 Hz, 1H), 6.52 (d, J = 3.5 Hz, 1H), 6.24 (d, J = 4.5 Hz, 1H), 3.92 (s, 1H), 2.60-2.54 (m, 2H), 2.20- 2.09 (m, 1H), 2.00 (d, J = 5.0 Hz, 1H), 1.94 (d, J = 12.3 Hz, 1H), 1.70-1.54 (m, 2H), 0.82-0.74 (m, 4H), 0.71 0.59 (m, 4H)

MS (ESI +) m / z 365 (M + H) ⁺

Example  247: N- (4- (4- (2- Cyanoacetamido ) Cyclohex -1-en-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2-cyanoacetamido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.54 (s, 1H), 8.31 (d, J = 7.3 Hz, 1H), 7.82 (s, 1H), 7.36-7.26 ( m, 1H), 6.53 (dd, J = 1.9, 3.6 Hz, 1H), 6.24 (s, 1H), 3.94 (s, 1H), 3.64 (s, 2H), 2.56 (d, J = 6.3 Hz, 3H ), 2.21-2.09 (m, 1H), 2.05-1.98 (m, 1H), 1.98-1.90 (m, 1H), 1.76-1.65 (m, 1H), 0.87-0.72 (m, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  248: N- (4- (4- (4,4,4- Trifluorobutaneamido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (4,4,4-trifluorobutanamido) Synthesis of cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.49 (s, 1H), 8.06 (d, J = 7.5 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H) , 7.31 (q, J = 3.0, 3.6 Hz, 1H), 6.52 (dd, J = 1.9, 3.6 Hz, 1H), 6.23 (d, J = 4.4 Hz, 1H), 3.94 (d, J = 10.0 Hz, 1H), 2.92 (d, J = 22.6 Hz, 1H), 2.74-2.65 (m, 2H), 2.55 (s, 3H), 2.38 (dd, J = 6.4, 8.7 Hz, 2H), 2.18-2.07 (m , 1H), 2.05-1.98 (m, 1H), 1.93 (dd, J = 4.9, 12.4 Hz, 1H), 1.67 (q, J = 9.7, 12.2 Hz, 1H), 1.25-1.19 (m, 4H), 0.86-0.74 (m, 4H)

MS (ESI +) m / z 421 (M + H) ⁺

Example  249: N- (4- (1- (1,1-dioxydotetrahydro-2H-thiopyran-4-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H -Pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1,1-dioxidotetrahydro-2H-thiopyran-4-carbonyl) -1,2, Synthesis of 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.54 (s, 1H), 7.87 (s, 1H), 7.35 (s, 1H), 6.57 (s, 1H), 6.34 ( d, J = 29.7 Hz, 1H), 4.38-3.97 (m, 3H), 3.75 (d, J = 15.9 Hz, 2H), 3.11 (d, J = 14.9 Hz, 5H), 2.64 (s, 2H), 2.02 (d, J = 20.0 Hz, 6H), 1.26-1.12 (m, 2H), 0.85-0.76 (m, 4H)

MS (ESI +) m / z 443 (M + H) ⁺

Example  250 N- (4- (1- (2- Cyanoacetyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.44 (s, 1H), 10.53 (s, 1H), 7.86 (s, 1H), 7.41-7.31 (m, 1H), 6.55 (s, 1H), 6.31 (d, J = 25.9 Hz, 1H), 4.26-4.04 (m, 4H), 3.77-3.67 (m, 1H), 3.59 (t, J = 5.3 Hz, 1H), 3.17 (s, 1H), 2.65 ( s, 1H), 2.02 (s, 1H), 0.84-0.78 (m, 4H)

MS (ESI +) m / z 350 (M + H) ⁺

Example  251: N- (4- (1- (2- (1,1- Dioxidothiomorpholino ) Acetyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2- (1,1-dioxidothiomorpholino) acetyl)- 1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamid)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.54 (s, 1H), 7.87 (s, 1H), 7.35 (t, J = 3.1 Hz, 1H), 6.56 (s, 1H), 6.33 (d, J = 24.9 Hz, 1H), 4.51-4.36 (m, 2H), 4.35-4.20 (m, 2H), 4.06-3.93 (m, 1H), 3.86-3.67 (m, 2H) , 3.64-3.48 (m, 2H), 3.21 (d, J = 14.0 Hz, 2H), 3.08 (d, J = 12.0 Hz, 3H), 2.02 (s, 1H), 0.80 (d, J = 8.0 Hz, 4H)

MS (ESI +) m / z 458 (M + H) ⁺

Example  252: N- (4- (1- (3- Cyanopropanoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-cyanopropanoyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (s, 1H), 7.87 (s, 1H), 7.34 (t, J = 3.0 Hz, 1H), 6.59-6.52 ( m, 1H), 6.33 (d, J = 21.2 Hz, 1H), 4.21 (s, 2H), 3.70 (dt, J = 30.9, 5.5 Hz, 2H), 2.82 (dt, J = 24.0, 6.8 Hz, 2H ), 2.70-2.59 (m, 4H), 2.01 (d, J = 6.2 Hz, 1H), 0.86-0.74 (m, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  253: N- (4- (1- (3,3,3- Trifluoropropanoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3,3,3-trifluoropropanoyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (d, J = 3.5 Hz, 1H), 7.86 (s, 1H), 7.34 (s, 1H), 6.55 (s, 1H), 6.31 (d, J = 27.5 Hz, 1H), 4.19 (s, 2H), 3.64 (p, J = 6.8, 6.0 Hz, 7H), 2.62 (s, 2H), 2.01 (s, 1H), 0.85-0.76 (m, 4H)

MS (ESI +) m / z 393 (M + H) ⁺

Example  254: N- (4- (1- (4,4,4- Trifluorobutanoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (4,4,4-trifluorobutanoyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.52 (s, 1H), 7.85 (s, 1H), 7.34 (s, 1H), 6.55 (s, 1H), 6.34 ( s, 1H), 4.19 (d, J = 6.5 Hz, 2H), 3.75 (s, 2H), 3.24 (d, J = 10.1 Hz, 4H), 2.65 (d, J = 27.0 Hz, 2H), 2.00 ( s, 1H), 0.78 (d, J = 11.5 Hz, 4H)

MS (ESI +) m / z 407 (M + H) ⁺

Example  255: N- (4- (8- (3- Cyanopropanoyl )-8- Azabicyclo [3.2.1] oct 2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (3-cyanopropanoyl) -8-azabicyclo [3.2.1] synthesis of oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 390 (M + H) ⁺

Example  256: N- (4- (8- ( Cyclopropanecarbonyl )-8- Azabicyclo [3.2.1] oct 2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (cyclopropanecarbonyl) -8-azabicyclo [3.2 .1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 377 (M + H) ⁺

Example  257: N- (4- (8- (2- Cyanoacetyl )-8- Azabicyclo [3.2.1] oct -2-en-3-yl) -1H-pyrrolo [2,3-b] -6-yl) cyclopropanecarboxamide (N- (4- (8- (2-cyanoacetyl) -8-azabicyclo [ 3.2.1] Synthesis of oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 376 (M + H) ⁺

Example  258: N- (4- (8- (4,4,4- Trifluorobutanoyl )-8- Azabicyclo [3.2.1] oct -2-en-3-yl) -1H-pyrrolo [2,3b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (4,4,4-trifluorobutanoyl) -8 -azabicyclo [3.2.1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 433 (M + H) ⁺

Example  259: N- (4- (1- (1- Cyanocyclopropane -1-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1-cyanocyclopropane-1-carbonyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 376 (M + H) ⁺

Example  260: N- (4- (1- (3,3- Difluorocyclobutane -1-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3,3-difluorocyclobutane-1-carbonyl) -1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53-11.35 (m, 1H), 10.53 (s, 1H), 7.86 (s, 1H), 7.34 (d, J = 2.8 Hz, 1H), 6.63- 6.48 (m, 1H), 6.38-6.24 (m, 1H), 4.19 (d, J = 8.8 Hz, 2H), 3.68 (dt, J = 5.6, 47.7 Hz, 2H), 2.81 (ddt, J = 5.7, 11.0, 21.2 Hz, 4H), 2.59 (s, 2H), 2.00 (d, J = 14.4 Hz, 1H), 0.85-0.73 (m, 4H)

MS (ESI +) m / z 401 (M + H) ⁺

Example  261: N- (4- (8- (3,3,3- Trifluoropropanoyl )-8- Azabicyclo [3.2.1] Oct 2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (3,3,3-trifluoropropanoyl) -8-azabicyclo [3.2.1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 419 (M + H) ⁺

Example  262: N- (4- (8- (2- Cyanoacetyl )-8- Azabicyclo [3.2.1] oct -2-en-3-yl) -1H-pyrrolo [2,3-b] -6-yl) cyclopropanecarboxamide (N- (4- (8- (2-cyanoacetyl) -8-azabicyclo [ 3.2.1] Synthesis of oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 376 (M + H) ⁺

Example  263: N- (4- (1- (2,2- Difluorocyclopropane -1-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2,2-difluorocyclopropane-1-carbonyl) -1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.68 (s, 1H), 8.06 (d, J = 2.3 Hz, 1H), 7.91 (d, J = 4.2 Hz, 1H), 6.94 (dd, J = 5.8, 4.1 Hz, 1H), 6.32 (s, 1H), 5.17 (q, J = 10.6 Hz, 1H), 4.56-4.28 (m, 1H), 4.28-4.12 (m, 1H), 3.93 (s, 1H ), 3.77 (t, J = 5.8 Hz, 2H), 2.75 (s, 1H), 2.38-2.29 (m, 1H), 2.23 (d, J = 11.8 Hz, 1H), 2.06-1.80 (m, 4H) , 0.86 (d, J = 5.7 Hz, 4H)

MS (ESI +) m / z 387 (M + H) ⁺

Example  264: N- (4- (1- ( Cyclopropanecarbonyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (cyclopropanecarbonyl) -1,2,3,6-tetrahydropyridin Synthesis of -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (s, 1H), 7.87 (s, 1H), 7.34 (dd, J = 2.5, 3.5 Hz, 1H), 6.56 ( dd, J = 1.9, 3.6 Hz, 1H), 6.35 (s, 1H), 4.32 (d, J = 110.2 Hz, 2H), 3.82 (d, J = 78.9 Hz, 2H), 2.65 (d, J = 9.9 Hz, 1H), 2.13-1.92 (m, 2H), 0.84-0.70 (m, 8H)

MS (ESI +) m / z 351 (M + H) ⁺

Example  265: N- (4- (1- (4- Cyanobutanoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (4-cyanobutanoyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (s, 1H), 7.86 (s, 1H), 7.37-7.30 (m, 1H), 6.56 (dd, J = 1.9 , 3.5 Hz, 1H), 6.33 (d, J = 17.7 Hz, 1H), 4.20 (dd, J = 3.2, 15.0 Hz, 2H), 3.70 (dt, J = 5.6, 18.5 Hz, 2H), 2.64-2.52 (m, 6H), 2.01 (q, J = 3.1, 3.7 Hz, 1H), 1.84 (p, J = 7.4 Hz, 2H), 0.86-0.77 (m, 4H)

MS (ESI +) m / z 378 (M + H) ⁺

Example  266: N- (4- (1-acryloyl-1,2,3,6- Tetrahydropyridine -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1-acryloyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6- yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (s, 1H), 7.87 (s, 1H), 7.34 (t, J = 3.0 Hz, 1H), 6.98-6.76 ( m, 1H), 6.56 (s, 1H), 6.34 (d, J = 24.5 Hz, 1H), 6.16 (d, J = 16.6 Hz, 1H), 5.72 (d, J = 10.2 Hz, 1H), 4.30 ( d, J = 40.6 Hz, 2H), 3.85-3.74 (m, 2H), 2.61 (s, 2H), 2.02 (s, 1H), 0.82-0.74 (m, 4H)

MS (ESI +) m / z 337 (M + H) ⁺

Example  267: N- (4- (1-(( 1S, 2S )-2- Cyanocyclopropane -One- Carbonyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] -6-yl) cyclopropanecarboxamide (N- (4- (1-((1S, 2S) -2-cyanocyclopropane-1-carbonyl ) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.54 (s, 1H), 7.88 (s, 1H), 7.35 (s, 1H), 6.57 (d, J = 2.4 Hz, 1H), 6.35 (s, 1H), 4.50 (d, J = 3.2 Hz, 1H), 4.19 (s, 1H), 4.00-3.87 (m, 1H), 3.83-3.64 (m, 1H), 3.03-2.80 (m, 1H), 2.10 (dt, J = 5.2, 9.7 Hz, 1H), 2.02 (s, 1H), 1.45 (s, 1H), 1.35 (d, J = 4.1 Hz, 1H), 0.86-0.73 ( m, 4H)

MS (ESI +) m / z 376 (M + H) ⁺

Example  268: N- (4- (1- (2- (1- Cyanocyclopropyl ) Acetyl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2- (1-cyanocyclopropyl) acetyl) -1, 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (s, 1H), 7.86 (s, 1H), 7.34 (t, J = 3.0 Hz, 1H), 6.56 (d, J = 4.1 Hz, 1H), 6.32 (d, J = 37.2 Hz, 1H), 4.21 (s, 1H), 4.14 (s, 1H), 3.74 (t, J = 5.6 Hz, 1H), 3.59 (t, J = 4.9 Hz, 1H), 2.79 (s, 1H), 2.74 (s, 1H), 2.61 (s, 1H), 2.05-1.96 (m, 2H), 1.18 (s, 1H), 0.94 (dd, J = 7.3, 4.8 Hz, 2H), 0.89-0.74 (m, 5H)

MS (ESI +) m / z 390 (M + H) ⁺

Example  269: N- (4- (1- (2- Cyanopropanoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanopropanoyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 364 (M + H) ⁺

Example  270: N- (4- (1- ( Boot -3- Enoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (but-3-enoyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.57 (s, 1H), 7.84 (s, 1H), 7.35 (t, J = 3.0 Hz, 1H), 6.56 (d, J = 2.7 Hz, 1H), 6.34 (d, J = 23.8 Hz, 1H), 6.02-5.85 (m, 1H), 5.15-5.08 (m, 2H), 4.25-4.14 (m, 2H), 3.24 (dd , J = 18.3, 6.7 Hz, 2H), 3.02 (d, J = 6.7 Hz, 1H), 2.69 (s, 2H), 2.06-1.95 (m, 2H), 0.86-0.78 (m, 4H)

MS (ESI +) m / z 351 (M + H) ⁺

Example  271: N- (4- (1- (2- Cyanobutanoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanobutanoyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 378 (M + H) ⁺

Example  272: N- (4- (1- (2,2,2- Trifluoroacetyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2,2,2-trifluoroacetyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 7.88 (s, 1H), 7.36 (t, J = 3.0 Hz, 1H), 6.57 (td, J = 1.8, 3.5 Hz, 1H), 6.46-6.31 (m, 1H), 4.42-4.28 (m, 2H), 3.85 (dt, J = 5.6, 10.9 Hz, 2H), 2.66 (d, J = 15.5 Hz , 2H), 2.02 (ddd, J = 3.4, 7.5, 14.4 Hz, 1H), 0.83-0.70 (m, 4H).

MS (ESI +) m / z 379 (M + H) ⁺

Example  273: N- (4- (1- (2- Methylcyclopropane -1-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-methylcyclopropane-1-carbonyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.56 (s, 1H), 7.88 (s, 1H), 7.40-7.26 (m, 1H), 6.56 (dd, J = 1.9 , 3.6 Hz, 1H), 6.35 (s, 1H), 4.44 (s, 1H), 4.16 (s, 1H), 3.90 (s, 1H), 3.70 (s, 1H), 2.65 (d, J = 12.4 Hz , 1H), 2.02 (s, 1H), 1.77 (d, J = 49.4 Hz, 1H), 1.26-1.09 (m, 5H), 0.95 (d, J = 6.2 Hz, 1H), 0.83-0.76 (m, 4H)

MS (ESI +) m / z 365 (M + H) ⁺

Example  274: N- (4- (1-(-2- Fluorocyclopropane -One- Carbonyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] -6-yl) cyclopropanecarboxamide (N- (4- (1- (2-fluorocyclopropane-1-carbonyl) -1,2, Synthesis of 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.54 (s, 1H), 7.86 (s, 1H), 7.33 (t, J = 3.0 Hz, 1H), 6.55 (t, J = 2.7 Hz, 1H), 6.33 (s, 1H), 4.74 (d, J = 5.4 Hz, 1H), 4.46 (s, 1H), 4.15 (s, 1H), 3.92 (s, 1H), 3.78- 3.58 (m, 1H), 2.71-2.61 (m, 2H), 2.00 (s, 1H), 1.43 (s, 1H), 1.18 (dt, J = 7.0, 13.0 Hz, 1H), 0.84-0.73 (m, 4H)

MS (ESI +) m / z 369 (M + H) ⁺

Example 275: 4 -(1- (2- Cyanoacetyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridine7-oxide (4- (1- (2-cyanoacetyl) -1,2,3,6 -tetrahydropyridin-4-yl) -6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridine 7- oxide ) Synthesis

MS (ESI +) m / z 366 (M + H) ⁺

Example  276: N- (4- (1- (2- (3,4-) Difluorophenyl ) Acetyl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] cyclopropane Carboxamide  (N- (4- (1- (2- (3,4-difluorophenyl) acetyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.45 (s, 1H), 10.56 (s, 1H), 7.87 (s, 1H), 7.42-7.30 (m, 3H), 7.10 (s, 1H), 6.53 (dd, J = 1.8, 3.5 Hz, 1H), 6.33 (d, J = 21.7 Hz, 1H), 4.30 (s, 1H), 4.20 (s, 1H), 3.82 (d, J = 17.6 Hz, 2H ), 3.75 (t, J = 6.4 Hz, 2H), 2.68 (d, J = 7.4 Hz, 2H), 2.02 (s, 1H), 0.87-0.76 (m, 4H)

MS (ESI +) m / z 437 (M + H) ⁺

Example  277: N- (4- (1- Isicotinoyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-isonicotinoyl-1,2,3,6-tetrahydropyridin-4 -yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 8.70 (d, J = 5.1 Hz, 2H), 7.88 (s, 1H), 7.53-7.43 ( m, 2H), 7.35 (d, J = 11.1 Hz, 1H), 6.64-6.51 (m, 1H), 6.32 (d, J = 82.1 Hz, 1H), 4.36 (s, 1H), 4.08 (s, 1H ), 3.91 (s, 1H), 3.51 (s, 1H), 2.63 (s, 2H), 2.02 (s, 1H), 0.85-0.74 (m, 4H)

MS (ESI +) m / z 388 (M + H) ⁺

Example  278: N- (4- (1- (furan-3-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (furan-3-carbonyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.45 (s, 1H), 10.56 (s, 1H), 8.15 (s, 1H), 7.89 (s, 1H), 7.80-7.72 (m, 1H), 7.43-7.27 (m, 1H), 6.76 (d, J = 1.9 Hz, 1H), 6.59 (s, 1H), 6.36 (s, 1H), 4.32 (s, 2H), 3.81 (s, 2H), 2.68 (d, J = 7.1 Hz, 2H), 2.01 (d, J = 8.1 Hz, 1H), 0.83-0.75 (m, 4H)

MS (ESI +) m / z 377 (M + H) ⁺

Example  279: N- (4- (1- (4- Fluorobenzoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (4-fluorobenzoyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.45 (s, 1H), 10.56 (s, 1H), 7.88 (s, 1H), 7.57 (dd, J = 5.5, 8.5 Hz, 2H), 7.38- 7.19 (m, 3H), 6.59 (s, 1H), 6.42 (s, 1H), 4.24 (d, J = 60.2 Hz, 2H), 3.68-3.52 (m, 2H), 2.66 (d, J = 24.6 Hz , 2H), 2.01 (s, 1H), 0.83-0.71 (m, 4H)

MS (ESI +) m / z 405 (M + H) ⁺

Example  280: N- (4- (1- (1- Methylpyrrolidine -3-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridine-6-cyclopropanecarboxamide (N- (4- (1- (1-methylpyrrolidine-3-carbonyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.45 (s, 1H), 10.55 (s, 1H), 7.86 (s, 1H), 7.35 (s, 1H), 6.56 (s, 1H), 6.34 ( d, J = 24.0 Hz, 1H), 4.22 (d, J = 32.6 Hz, 2H), 3.71 (d, J = 5.4 Hz, 2H), 2.67 (s, 2H), 2.36-2.21 (m, 4H), 2.00 (s, 3H), 0.88-0.71 (m, 4H)

MS (ESI +) m / z 394 (M + H) ⁺

Example  281: N- (4- (1- ( Dimethyl glycyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (dimethylglycyl) -1,2,3,6-tetrahydropyridin Synthesis of -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.47 (s, 1H), 10.57 (s, 1H), 7.88 (d, J = 4.4 Hz, 1H), 7.36 (s, 1H), 6.56 (d, J = 3.6 Hz, 1H), 6.40-6.28 (m, 1H), 4.20 (d, J = 37.1 Hz, 4H), 3.78 (s, 1H), 3.60 (s, 1H), 2.77 (s, 6H), 2.62 (d, J = 36.3 Hz, 3H), 2.05-1.97 (m, 1H), 0.79 (s, 4H)

MS (ESI +) m / z 368 (M + H) ⁺

Example  282: N- (4- (1- (2- (trifluoromethyl) cyclopropane-1-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [ 2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2- (trifluoromethyl) cyclopropane-1-carbonyl) -1,2,3,6-tetrahydropyridin-4 -yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.45 (s, 1H), 10.55 (s, 1H), 7.87 (s, 1H), 7.35 (s, 1H), 6.56 (s, 1H), 6.34 ( s, 1H), 4.47 (d, J = 16.4 Hz, 1H), 4.20 (s, 1H), 3.92 (s, 1H), 3.64 (s, 2H), 2.67-2.61 (m, 2H), 2.26 (s , 1H), 2.01 (s, 1H), 0.78 (d, J = 9.3 Hz, 4H)

MS (ESI +) m / z 419 (M + H) ⁺

Example  283: N- (4- (1- (2- Cyanoacetyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridine-6-cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -3-methyl-1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.57 (s, 1H), 7.84 (d, J = 10.2 Hz, 1H), 7.34 (d, J = 3.1 Hz, 1H) , 6.48 (dd, J = 1.8, 3.7 Hz, 1H), 6.17-6.03 (m, 1H), 4.31-4.01 (m, 6H), 3.96-3.62 (m, 2H), 3.02 (m J = 36.6 Hz, 1H), 2.02 (s, 1H), 0.88 (s, 3H), 0.84-0.73 (m, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  284: N- (4- (1- (3- Cyanopropanoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridine-6-cyclopropanecarboxamide (N- (4- (1- (3-cyanopropanoyl) -3-methyl-1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.56 (s, 1H), 7.85 (d, J = 5.5 Hz, 1H), 7.34 (d, J = 3.5 Hz, 1H) , 6.49 (dt, J = 2.0, 3.5 Hz, 1H), 6.11 (d, J = 15.7 Hz, 1H), 4.31 (d, J = 24.5 Hz, 1H), 4.14-3.90 (m, 2H), 3.57 ( d, J = 4.5 Hz, 2H), 3.00 (d, J = 27.7 Hz, 2H), 2.85 (dd, J = 7.7, 15.5 Hz, 4H), 2.02 (s, 1H), 0.88 (d, J = 10.7 Hz, 3H), 0.82-0.76 (m, 4H)

MS (ESI +) m / z 378 (M + H) ⁺

Example  285: N- (4- (1- (4- Cyanobutanoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridine-6-cyclopropanecarboxamide (N- (4- (1- (4-cyanobutanoyl) -3-methyl-1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.56 (s, 1H), 7.84 (d, J = 5.1 Hz, 1H), 7.33 (s, 1H), 6.49 (s, 1H), 6.11 (d, J = 10.4 Hz, 1H), 4.44-4.24 (m, 1H), 3.93 (d, J = 17.1 Hz, 1H), 3.66-3.56 (m, 2H), 2.98 (d, J = 26.6 Hz, 1H), 2.68 (s, 4H), 2.04 (d, J = 19.1 Hz, 1H), 1.84 (p, J = 6.3, 6.9 Hz, 2H), 0.93-0.84 (m, 3H), 0.83 0.71 (m, 4H)

MS (ESI +) m / z 392 (M + H) ⁺

Example  286: N- (4- (1- (1,2,5- Oxadiazole -3-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridine-6-cyclopropanecarboxamide (N- (4- (1- (1,2,5-oxadiazole-3-carbonyl) -1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (s, 1H), 10.57 (s, 1H), 9.32 (d, J = 10.0 Hz, 1H), 7.89 (s, 1H), 7.36 (dt, J = 6.3, 3.2 Hz, 1H), 6.57 (ddd, J = 8.5, 3.6, 1.9 Hz, 1H), 6.36 (d, J = 47.7 Hz, 1H), 4.42 (d, J = 3.9 Hz, 2H), 3.96 (t, J = 5.6 Hz, 1H), 3.84 (t, J = 5.6 Hz, 1H), 2.68 (d, J = 6.7 Hz, 2H), 2.04-1.99 (m, 1H), 0.82-0.75 (m , 4H)

MS (ESI +) m / z 379 (M + H) ⁺

Example  287: N- (4- (1- ( Ixoxazole -4-carbonyl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (isoxazole-4-carbonyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 9.46 (s, 1H), 8.94 (s, 1H), 7.89 (s, 1H), 7.36 ( s, 1H), 6.58 (d, J = 18.3 Hz, 1H), 6.34 (d, J = 47.3 Hz, 1H), 4.35 (d, J = 34.0 Hz, 2H), 3.81 (d, J = 39.9 Hz, 2H), 2.73 (s, 1H), 2.61 (s, 1H), 2.00 (d, J = 13.2 Hz, 1H), 0.85-0.74 (m, 4H)

MS (ESI +) m / z 378 (M + H) ⁺

Example  288: N- (4- (1- ( Ixoxazole -5-carbonyl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (isoxazole-5-carbonyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 8.79 (t, J = 2.9 Hz, 1H), 7.89 (d, J = 4.7 Hz, 1H) , 7.36 (s, 1H), 7.07-7.00 (m, 1H), 6.58 (d, J = 13.4 Hz, 1H), 6.35 (d, J = 45.2 Hz, 1H), 4.36 (s, 2H), 3.91 ( s, 1H), 3.75 (d, J = 6.0 Hz, 1H), 2.70 (s, 1H), 2.64 (s, 1H), 2.00 (d, J = 9.2 Hz, 1H), 0.85-0.76 (m, 4H )

MS (ESI +) m / z 378 (M + H) ⁺

Example  289: N- (4- (1- (2- Cyanoacetyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -5-methyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -5-methyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.50 (s, 1H), 10.12 (s, 1H), 7.37 (t, J = 2.9 Hz, 1H), 6.31 (s, 1H), 5.69 (d, J = 7.0 Hz, 1H), 4.20-4.07 (m, 4H), 3.62 (t, J = 5.8 Hz, 2H), 2.42 (s, 1H), 2.37-2.26 (m, 1H), 2.11 (s, 3H ), 1.92-1.80 (m, 1H), 0.79 (d, J = 6.0 Hz, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  290: N- (5- methyl -4- (1- (3,3,3- Trifluoropropanoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridine-6-cyclopropanecarboxamide (N- (5-methyl-4- (1- (3,3,3-trifluoropropanoyl) -1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.04 (s, 1H), 7.35 (t, J = 3.0 Hz, 1H), 6.26 (d, J = 2.5 Hz, 1H) , 5.68 (d, J = 6.8 Hz, 1H), 4.26-4.12 (m, 2H), 3.84-3.66 (m, 4H), 2.41 (s, 1H), 2.30 (s, 1H), 2.09 (s, 3H ), 1.83 (q, J = 6.3 Hz, 1H), 0.76 (d, J = 6.2 Hz, 4H)

MS (ESI +) m / z 407 (M + H) ⁺

Example  291: N- (4- (1- (thiazole-4-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (thiazole-4-carbonyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.56 (s, 1H), 9.22 (s, 1H), 8.24 (d, J = 2.0 Hz, 1H), 7.89 (s, 1H), 7.35 (s, 1H), 6.57 (d, J = 14.9 Hz, 1H), 6.37 (d, J = 60.7 Hz, 1H), 4.40 (d, J = 35.2 Hz, 2H), 3.88 (d, J = 19.6 Hz, 2H), 2.65 (s, 2H), 2.01 (d, J = 5.7 Hz, 1H), 1.24 (m, 2H), 0.80 (m, 2H)

MS (ESI +) m / z 394 (M + H) ⁺

Example  292: N- (4- (1- ( Isothiazole -4-carbonyl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (isothiazole-4-carbonyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 8.65 (d, J = 1.8 Hz, 1H), 7.89 (s, 1H), 7.77 (s, 1H), 7.35 (s, 1H), 6.60 (s, 1H), 6.35 (d, J = 53.1 Hz, 1H), 4.36 (d, J = 3.1 Hz, 2H), 3.91 (s, 1H), 3.74 ( s, 1H), 2.71-2.65 (m, 2H), 2.02 (dd, J = 8.9, 4.0 Hz, 1H), 1.25 (m, 2H), 0.87-0.73 (m, 2H)

MS (ESI +) m / z 394 (M + H) ⁺

Example  293: N- (4- (1- (4- Cyanobenzoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (4-cyanobenzoyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.56 (s, 1H), 7.96 (d, J = 7.8 Hz, 2H), 7.88 (s, 1H), 7.69 (d, J = 7.9 Hz, 2H), 7.36 (s, 1H), 6.57 (d, J = 30.7 Hz, 1H), 6.32 (d, J = 87.2 Hz, 1H), 4.35 (s, 1H), 3.99 (d, J = 68.8 Hz, 2H), 3.50 (s, 1H), 2.62 (s, 2H), 2.04-1.96 (m, 1H), 0.80 (d, J = 5.2 Hz, 4H)

MS (ESI +) m / z 412 (M + H) ⁺

Example  294: N- (4- (1- (2- Cyanoacetyl ) -3-ethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -3-ethyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.56 (s, 1H), 7.83 (d, J = 10.8 Hz, 1H), 7.34 (s, 1H), 6.48 (d, J = 3.2 Hz, 1H), 6.10 (d, J = 22.6 Hz, 1H), 4.34-4.19 (m, 2H), 4.04 (dd, J = 9.2, 18.5 Hz, 2H), 3.62-3.57 (m, 1H ), 2.76 (s, 1H), 2.00 (d, J = 12.4 Hz, 1H), 1.28 (s, 2H), 1.03 (d, J = 6.2 Hz, 3H), 0.87-0.73 (m, 7H)

MS (ESI +) m / z 378 (M + H) ⁺

Example  295: N- (4- (1- (3- Cyanopropanoyl ) -3-ethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-cyanopropanoyl) -3-ethyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.56 (s, 1H), 7.84 (d, J = 5.5 Hz, 1H), 7.33 (s, 1H), 6.49 (d, J = 2.9 Hz, 1H), 6.13 (d, J = 23.5 Hz, 1H), 4.50-4.26 (m, 2H), 3.98 (dd, J = 19.2, 50.3 Hz, 1H), 3.76-3.48 (m, 3H ), 2.87 (s, 2H), 2.73 (d, J = 6.4 Hz, 2H), 2.00 (d, J = 12.8 Hz, 1H), 1.36-1.14 (m, 3H), 0.98-0.68 (m, 7H)

MS (ESI +) m / z 392 (M + H) ⁺

Example  296: N- (4- (1- (2- Cyanoacetyl ) -5- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -5-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.57 (s, 1H), 7.67 (s, 1H), 7.31 (t, J = 3.0 Hz, 1H), 6.24 (tt, J = 1.5, 3.3 Hz, 1H), 4.14 (dd, J = 1.2, 3.5 Hz, 2H), 4.07-3.94 (m, 2H), 3.70 (t, J = 5.7 Hz, 1H), 3.57 (t, J = 5.7 Hz, 1H), 2.34 (s, 1H), 2.05-1.95 (m, 1H), 1.52 (s, 3H), 1.24 (d, J = 8.3 Hz, 1H), 0.83-0.75 (m, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  297: N- (4- (1- (2- Bromoacetyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-bromoacetyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 404 (M + H) ⁺

Example  298: N- (4- (1- (2- Chloroacetyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-chloroacetyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 359, 361 (M + H) ⁺

Example  299: N- (4- (1- (2- Cyanoacetyl ) -3,3-dimethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -3,3-dimethyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.56 (s, 1H), 7.73 (d, J = 7.5 Hz, 1H), 7.28 (s, 1H), 6.30 (s, 1H), 5.67-5.54 (m, 1H), 4.19-4.06 (m, 4H), 3.48 (s, 2H), 2.01 (s, 1H), 1.01 (dd, J = 3.7, 13.5 Hz, 6H), 0.80 (d, J = 5.3 Hz, 4H)

MS (ESI +) m / z 378 (M + H) ⁺

Example  300: N- (4- (1- (3- Cyanopropanoyl ) -3,3-dimethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-cyanopropanoyl) -3,3-dimethyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.56 (s, 1H), 7.74 (d, J = 8.2 Hz, 1H), 7.28 (s, 1H), 6.34-6.24 ( m, 1H), 5.60 (d, J = 10.1 Hz, 1H), 4.13 (dd, J = 3.3, 14.9 Hz, 2H), 3.50-3.44 (m, 2H), 2.82 (d, J = 3.8 Hz, 2H ), 2.67 (d, J = 4.4 Hz, 2H), 2.01 (s, 1H), 1.03 (s, 3H), 0.99 (s, 3H), 0.81-0.74 (m, 4H)

MS (ESI +) m / z 392 (M + H) ⁺

Example  301: N- (4- (1- (2- Cyanoacetyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) furan-2-carboxamide (N- (4- (1- (2-cyanoacetyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) furan-2-carboxamide)

MS (ESI +) m / z 376 (M + H) ⁺

Example  302: N- (4- (5- (3- Cyanopropanoyl ) -5- Azaspiro [2.5] Oct -7-en-8-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (5- (3-cyanopropanoyl) -5-azaspiro [2.5] oct-7-en-8-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (s, 1H), 10.59-10.52 (m, 1H), 7.55 (d, J = 8.5 Hz, 1H), 7.30 (q, J = 3.0 Hz, 1H), 6.27 (ddd, J = 10.1, 3.5, 1.9 Hz, 1H), 5.69 (dt, J = 7.0, 3.3 Hz, 1H), 4.23 (dd, J = 11.8, 3.2 Hz, 2H), 3.63 (dt , J = 6.6, 3.3 Hz, 2H), 3.57 (d, J = 19.1 Hz, 2H), 3.21-3.09 (m, 2H), 2.81 (dt, J = 23.9, 6.8 Hz, 2H), 2.67 (t, J = 6.3 Hz, 2H), 2.00 (d, J = 7.2 Hz, 1H), 0.81-0.76 (m, 4H)

MS (ESI +) m / z 390 (M + H) ⁺

Example  303: N- (4- (5- (2- Cyanoacetyl ) -5- Azaspiro [2.5] Oct -7-en-8-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (5- (2-cyanoacetyl) -5-azaspiro [2.5] oct-7-en-8-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.53 (s, 1H), 7.86 (d, J = 2.4 Hz, 1H), 7.35 (t, J = 3.0 Hz, 1H) , 6.55 (dd, J = 3.5, 1.8 Hz, 1H), 6.31 (d, J = 26.1 Hz, 1H), 4.21-4.17 (m, 1H), 4.13 (d, J = 23.2 Hz, 3H), 3.72 ( t, J = 5.6 Hz, 1H), 3.59 (t, J = 5.5 Hz, 1H), 2.64 (s, 2H), 2.55 (s, 1H), 2.01 (d, J = 4.8 Hz, 1H), 0.83- 0.77 (m, 4H)

MS (ESI +) m / z 376 (M + H) ⁺

Example  304: (S) -N- (4- (1- (2- Cyanoacetyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2-cyanoacetyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.57 (s, 1H), 7.84 (d, J = 10.2 Hz, 1H), 7.34 (d, J = 3.1 Hz, 1H) , 6.48 (dd, J = 1.8, 3.7 Hz, 1H), 6.17-6.03 (m, 1H), 4.31-4.01 (m, 6H), 3.96-3.62 (m, 2H), 3.02 (m J = 36.6 Hz, 1H), 2.02 (s, 1H), 0.88 (s, 3H), 0.84-0.73 (m, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  305: (R) -N- (4- (1- (2- Cyanoacetyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((R) -N- (4- (1- (2-cyanoacetyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.57 (s, 1H), 7.84 (d, J = 10.2 Hz, 1H), 7.34 (d, J = 3.1 Hz, 1H) , 6.48 (dd, J = 1.8, 3.7 Hz, 1H), 6.17-6.03 (m, 1H), 4.31-4.01 (m, 6H), 3.96-3.62 (m, 2H), 3.02 (m J = 36.6 Hz, 1H), 2.02 (s, 1H), 0.88 (s, 3H), 0.84-0.73 (m, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  306: N- (4- (3- methyl -1- (2- Methylthiazole -5-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (2-methylthiazole-5-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.03 (s, 1H), 7.85 (s, 1H), 7.33 (d, J = 3.5 Hz, 1H), 6.51 (s, 1H), 6.12 (s, 1H), 4.51 (d, J = 18.2 Hz, 1H), 4.25 (s, 1H), 3.83 (s, 2H), 3.07 (s, 1H), 2.70 (d, J = 2.8 Hz, 3H), 2.01 (d, J = 8.8 Hz, 1H), 0.90 (d, J = 6.7 Hz, 3H), 0.86-0.74 (m, 4H)

MS (ESI +) m / z 422 (M + H) ⁺

Example  307: N- (4- (1- (2,4-dimethylthiazole-5-carbonyl) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2,4-dimethylthiazole-5-carbonyl) -3 -methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 7.83 (s, 1H), 6.48 (s, 1H), 6.11 (s, 1H), 4.41 ( s, 1H), 4.09 (d, J = 18.6 Hz, 1H), 3.66 (s, 2H), 3.01 (s, 1H), 2.64 (d, J = 3.3 Hz, 3H), 2.32 (d, J = 3.4 Hz, 3H), 2.02 (s, 1H), 0.86 (d, J = 6.5 Hz, 3H), 0.78 (d, J = 9.6 Hz, 4H)

MS (ESI +) m / z 436 (M + H) ⁺

Example  308: N- (4- (3- methyl -1- (4- Methylthiazole -5-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (4-methylthiazole-5-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 9.12 (d, J = 2.1 Hz, 1H), 7.84 (d, J = 2.6 Hz, 1H) , 7.33 (q, J = 2.9 Hz, 1H), 6.48 (dt, J = 4.2, 2.0 Hz, 1H), 6.12 (s, 1H), 4.51 (s, 1H), 4.09 (d, J = 18.1 Hz, 1H), 3.74-3.59 (m, 1H), 3.01 (s, 1H), 2.41 (d, J = 2.3 Hz, 3H), 2.02 (tt, J = 8.8, 5.2 Hz, 1H), 0.94-0.83 (m , 3H), 0.82-0.74 (m, 4H)

MS (ESI +) m / z 422 (M + H) ⁺

Example  309: N- (4- (1- (2- Fluoroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-fluoroisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.37 (d, J = 5.1 Hz, 1H), 7.83 (d, J = 11.6 Hz, 1H) , 7.44 (s, 1H), 7.33 (s, 2H), 6.50 (d, J = 14.2 Hz, 1H), 6.08 (d, J = 71.4 Hz, 1H), 4.54 (d, J = 19.5 Hz, 1H) , 4.11 (d, J = 49.6 Hz, 2H), 3.60 (d, J = 13.1 Hz, 1H), 2.02 (s, 1H), 0.95 (d, J = 6.8 Hz, 1H), 0.84-0.73 (m, 6H)

MS (ESI +) m / z 420 (M + H) ⁺

Example  310: N- (4- (1- (2- Chloroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-chloroisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 12.1 Hz, 1H) , 7.65 (d, J = 7.4 Hz, 1H), 7.51 (s, 1H), 7.32 (d, J = 8.5 Hz, 1H), 6.50 (d, J = 11.5 Hz, 1H), 6.08 (d, J = 67.3 Hz, 1H), 4.58-4.10 (m, 1H), 4.05 (s, 1H), 3.60 (d, J = 12.9 Hz, 1H), 3.02 (d, J = 41.1 Hz, 1H), 2.01 (s, 1H), 0.94 (d, J = 6.6 Hz, 1H), 0.86-0.74 (m, 6H).

MS (ESI +) m / z 436, 438 (M + H) ⁺

Example  311: N- (4- (1- (3,4- Difluorobenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3,4-difluorobenzoyl) -3-methyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.67-7.49 (m, 3H), 7.33 (s, 2H), 6.50 (s, 1H), 4.12 (s, 2H), 3.63 (d, J = 12.5 Hz, 1H), 3.01 (s, 1H), 2.01 (s, 1H), 0.92 (s, 1H), 0.86-0.74 (m, 6 H).

MS (ESI +) m / z 437 (M + H) ⁺

Example  312: N- (4- (1- (3- Fluoro -4- Methoxybenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-fluoro-4-methoxybenzoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.39-7.23 (m, 4H), 6.49 (s, 1H), 6.10 (s, 1H), 4.13 (d, J = 18.7 Hz, 1H), 3.65 (d, J = 11.9 Hz, 1H), 3.02 (s, 1H), 2.02 (s, 1H), 0.92-0. 68 (m, 7 H).

MS (ESI +) m / z 449 (M + H) ⁺

Example  313: N- (4- (3- methyl -1- (1H-pyrrole-2-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (1H-pyrrole-2-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 11.42 (s, 1H), 10.55 (s, 1H), 7.86 (s, 1H), 7.32 (s, 1H), 6.91 ( s, 1H), 6.62 (s, 1H), 6.56-6.47 (m, 1H), 6.16 (s, 2H), 4.59 (d, J = 19.0 Hz, 1H), 4.30 (d, J = 19.2 Hz, 1H ), 4.08-3.96 (m, 1H), 3.06 (s, 1H), 2.02 (s, 1H), 0.92 (d, J = 6.7 Hz, 3H), 0.79 (s, 4H)

MS (ESI +) m / z 390 (M + H) ⁺

Example  314: N- (4- (1- (3- Fluoroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-fluoroisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.74 (s, 1H), 8.62-8.47 (m, 1H), 7.84 (d, J = 14.4 Hz, 1H), 7.57 (d, J = 5.3 Hz, 1H), 7.34 (d, J = 5.1 Hz, 1H), 6.49 (d, J = 10.0 Hz, 1H), 6.09 (d, J = 71.3 Hz, 1H), 4.17 (t, J = 19.7 Hz, 1H), 3.99 (s, 1H), 3.60 (d, J = 13.8 Hz, 1H), 3.01 (d, J = 56.3 Hz, 1H), 2.02 (s, 1H), 0.95 (d, J = 6.8 Hz, 1H), 0.79 (d, J = 7.4 Hz, 6H)

MS (ESI +) m / z 420 (M + H) ⁺

Example  315: N- (4- (1- (3- (2- (3,5-dioxomorpholino) ethyl) benzoyl) -3-methyl-1,2,3,6-tetrahydropyridine-4- Yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (2- (3,5-dioxomorpholino) ethyl) benzoyl ) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.81 (d, J = 17.3 Hz, 1H), 7.40 (t, J = 7.7 Hz, 1H) , 7.30 (d, J = 9.5 Hz, 4H), 6.50 (s, 1H), 6.09 (d, J = 71.6 Hz, 1H), 4.05 (d, J = 28.5 Hz, 2H), 3.91 (t, J = 7.4 Hz, 3H), 3.62 (dd, J = 13.1, 4.2 Hz, 1H), 3.38 (q, J = 7.0 Hz, 2H), 2.98 (s, 1H), 2.84 (t, J = 7.4 Hz, 2H) , 2.01 (d, J = 5.1 Hz, 1H), 1.09 (t, J = 7.0 Hz, 2H), 0.93 (s, 1H), 0.89-0.69 (m, 7H)

MS (ESI +) m / z 542 (M + H) ⁺

Example  316: N- (4- (3- methyl -1- (3- ( Phenylamino ) Benzoyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane Carboxamide  (N- (4- (3-methyl-1- (3- (phenylamino) benzoyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.55 (s, 1H), 9.20 (s, 1H), 8.18 (d, J = 4.9 Hz, 1H), 7.84 (s, 1H), 7.58 (ddd, J = 8.7, 7.1, 2.0 Hz, 1H), 7.37-7.29 (m, 2H), 6.94 (d, J = 7.6 Hz, 1H), 6.84 (d, J = 8.3 Hz, 1H ), 6.76 (dd, J = 7.0, 4.9 Hz, 1H), 6.49 (s, 1H), 4.46 (s, 1H), 4.27-4.05 (m, 2H), 3.67 (s, 1H), 3.04 (s, 1H), 2.02 (s, 1H), 0.88-0.69 (m, 7H)

MS (ESI +) m / z 492 (M + H) ⁺

Example  317: N- (4- (1- (6- (2,4-difluorophenyl) -2-oxo-1,2-dihydropyridine-3-carbonyl) -3-methyl-1,2, 3,6-tetrahydropyridin-4-yl} -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (6- (2, 4-difluorophenyl) -2-oxo-1,2-dihydropyridine-3-carbonyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 8.37 (d, J = 7.5 Hz, 1H), 7.84-7.75 (m, 2H), 7.52-7.41 (m, 2H), 7.36-7.20 (m, 3H), 6.88 (dd, J = 7.6, 1.5 Hz, 1H), 4.20-4.05 (m, 1H), 4.01 (p, J = 6.6 Hz, 1H), 3.49 (dt, J = 14.8, 6.9 Hz, 1H), 3.15 (q, J = 9.1 Hz, 1H), 2.07-1.99 (m, 1H), 1.94 (q, J = 12.1, 10.2 Hz, 1H), 1.25-1.17 (m, 3H ), 0.81 (td, J = 14.7, 12.6, 5.0 Hz, 4H)

MS (ESI +) m / z 530 (M + H) ⁺

Example  318: methyl 1- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-methyl-1,2,3,6-tetra Hydropyridine-1-carbonyl) cyclobutane-1-carboxylate ( methyl  1- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-methyl-1,2,3,6-tetrahydropyridine-1-carbonyl) cyclobutane-1 -carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.54 (s, 1H), 7.82 (d, J = 3.4 Hz, 1H), 7.39-7.26 (m, 1H), 6.45 ( d, J = 15.8 Hz, 1H), 6.06 (d, J = 43.3 Hz, 1H), 4.32-4.00 (m, 2H), 2.93 (s, 1H), 2.07-1.90 (m, 3H), 1.82 (s , 1H), 1.31-1.19 (m, 1H), 0.98-0.69 (m, 10H)

MS (ESI +) m / z 437 (M + H) ⁺

Example  319: Methyl 1- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-methyl-1,2,3,6-tetra Hydropyridine-1-carbonyl) cyclopropane-1-carboxylate ( methyl  1- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-methyl-1,2,3,6-tetrahydropyridine-1-carbonyl) cyclopropane-1 -carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.55 (s, 1H), 7.84 (d, J = 7.6 Hz, 1H), 7.41-7.26 (m, 1H), 6.48 ( s, 1H), 6.11 (d, J = 6.0 Hz, 1H), 4.28 (t, J = 20.9 Hz, 2H), 4.06 (d, J = 15.8 Hz, 2H), 3.68 (d, J = 8.6 Hz, 5H), 2.99 (d, J = 27.0 Hz, 1H), 2.02 (s, 1H), 1.40 (q, J = 11.2, 7.4 Hz, 4H), 1.32-1.21 (m, 2H), 0.88 (t, J = 7.4 Hz, 4H), 0.84-0.74 (m, 4H)

MS (ESI +) m / z 423 (M + H) ⁺

Example  320: Methyl3 -(4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3-methyl-3,6-dihydropyridin-1 (2H) -yl) -2-methyl-3-oxopropanoate (methyl 3- (4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3-b] pyridin -4- yl ) -3-methyl-3,6-dihydropyridin-1 (2H) -yl) -2-methyl-3-oxopropanoate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 7.85 (s, 1H), 7.34 (s, 1H), 6.48 (d, J = 8.4 Hz, 1H), 6.12 (d, J = 16.1 Hz, 1H), 4.21-3.97 (m, 6H), 3.68 (d, J = 19.0 Hz, 1H), 3.00 (s, 1H), 2.03 (s, 1H), 1.26 (dd, J = 7.6, 4.2 Hz, 4H), 0.87-0.74 (m, 7H)

MS (ESI +) m / z 411 (M + H) ⁺

Example  321: N- (4- (1- (6- (tert-butyl) -2-oxo-1,2-dihydropyridine-3-carbonyl) -3-methyl-1,2,3,6-tetra Hydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (6- (tert-butyl) -2- oxo-1,2-dihydropyridine-3-carbonyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.62 (s, 1H), 11.41 (s, 1H), 10.54 (s, 1H), 7.83 (d, J = 12.1 Hz, 1H), 7.48 (t, J = 6.5 Hz, 1H), 7.36-7.25 (m, 1H), 6.48 (s, 1H), 6.09 (d, J = 37.7 Hz, 2H), 4.26 (dd, J = 94.3, 20.9 Hz, 1H), 4.05 (s, 1H), 3.60-3.41 (m, 1H), 3.26 (dd, J = 13.0, 5.2 Hz, 1H), 3.04 (d, J = 24.5 Hz, 1H), 2.00 (d, J = 13.7 Hz , 1H), 1.28 (s, 9H), 0.84-0.72 (m, 7H)

MS (ESI +) m / z 474 (M + H) ⁺

Example  322: N- (4- (1- (6- (4-fluorophenyl) -2-oxo-1,2-dihydropyridine-3-carbonyl) -3-methyl-1,2,3,6 -Tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (6- (4-fluorophenyl)- 2-oxo-1,2-dihydropyridine-3-carbonyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 12.21 (s, 1H), 11.42 (s, 1H), 10.54 (s, 1H), 8.00-7.80 (m, 3H), 7.64 (d, J = 7.4 Hz, 1H), 7.35 (t, J = 8.6 Hz, 3H), 6.49 (t, J = 2.0 Hz, 1H), 6.10 (d, J = 44.8 Hz, 1H), 4.26-4.03 (m, 2H), 3.69-3.44 (m, 2H), 3.05 (s, 1H), 2.02 (s, 1H), 0.91-0.70 (m, 7H)

MS (ESI +) m / z 512 (M + H) ⁺

Example  323: N- (4- (1- (3-fluoro-4-((2-morpholinoethyl) amino) benzoyl) -3-methyl-1,2,3,6-tetrahydropyridine-4- Yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-fluoro-4-((2-morpholinoethyl) amino) benzoyl ) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.43-7.28 (m, 1H), 7.25-7.12 (m, 2H), 6.78 (t, J = 8.6 Hz, 1H), 6.56-6.44 (m, 1H), 6.10 (s, 1H), 5.64 (s, 1H), 4.42-4.07 (m, 2H), 3.69 (s, 2H), 3.64-3.52 ( m, 4H), 3.26 (t, J = 6.2 Hz, 2H), 3.03 (s, 1H), 2.43 (s, 2H), 2.11-1.94 (m, 1H), 0.85 (d, J = 6.8 Hz, 4H ), 0.83-0.74 (m, 4H).

MS (ESI +) m / z 547 (M + H) ⁺

Example  324: N- (4- (1- (5- Bromonicotinyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (5-bromonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.82 (d, J = 2.4 Hz, 1H), 8.68 (d, J = 4.6 Hz, 1H) , 8.22 (d, J = 8.6 Hz, 1H), 7.84 (d, J = 8.6 Hz, 1H), 7.33 (s, 1H), 6.50 (d, J = 12.8 Hz, 1H), 6.09 (d, J = 63.9 Hz, 1H), 4.16 (d, J = 15.0 Hz, 2H), 3.64 (s, 1H), 3.36 (d, J = 7.5 Hz, 1H), 3.04 (d, J = 25.2 Hz, 1H), 2.00 (d, J = 14.1 Hz, 1H), 0.89-0.71 (m, 7H).

MS (ESI +) m / z 480, 482 (M + H) ⁺

Example  325: N- (4- (1- (2,3-dihydrobenzo [b] [1,4] dioxine-6-carbonyl) -3-methyl-1,2,3,6-tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2,3-dihydrobenzo [b] [1,4 ] dioxine-6-carbonyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.82 (s, 1H), 7.35-7.25 (m, 1H), 7.00-6.88 (m, 3H ), 6.49 (s, 1H), 6.10 (s, 1H), 4.27 (s, 4H), 4.17-4.04 (m, 1H), 3.72-3.57 (m, 1H), 3.00 (s, 1H), 2.01 ( td, J = 7.8, 7.4, 3.7 Hz, 1H), 0.85 (s, 3H), 0.84-0.76 (m, 4H)

MS (ESI +) m / z 459 (M + H) ⁺

Example  326: N- (4- (1- ( Benzo [d] [1,3] dioxoles -5-carbonyl) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (benzo [d] [1,3] dioxole-5-carbonyl ) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.54 (s, 1H), 7.82 (s, 1H), 7.32 (t, J = 3.0 Hz, 1H), 7.04 (s, 1H), 6.98 (d, J = 2.4 Hz, 2H), 6.49 (d, J = 3.4 Hz, 1H), 6.09 (s, 3H), 4.18-4.02 (m, 1H), 3.69-3.57 (m, 1H ), 3.01 (s, 1H), 2.01 (td, J = 7.4, 3.6 Hz, 1H), 0.84 (s, 3H), 0.81-0.75 (m, 4H)

MS (ESI +) m / z 445 (M + H) ⁺

Example  327: N- (4- (1- (1H-indole-6-carbonyl) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1H-indole-6-carbonyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (d, J = 2.8 Hz, 1H), 11.31 (s, 1H), 10.55 (s, 1H), 7.88-7.82 (m, 1H), 7.61 ( d, J = 8.1 Hz, 1H), 7.51 (d, J = 1.4 Hz, 1H), 7.47 (t, J = 2.7 Hz, 1H), 7.32 (t, J = 3.0 Hz, 1H), 7.10 (dd, J = 8.1, 1.5 Hz, 1H), 6.49 (t, J = 2.5 Hz, 2H), 6.12 (s, 1H), 4.22-4.11 (m, 1H), 3.75-3.65 (m, 1H), 3.03 (s , 1H), 2.02 (td, J = 8.6, 7.9, 4.2 Hz, 1H), 0.88 (s, 3H), 0.83-0.74 (m, 4H)

MS (ESI +) m / z 440 (M + H) ⁺

Example  328: N- (4- (3- methyl -1- (1H- Pyrrolo [2,3-b] pyridine -4-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- ( 4- (3-methyl-1- (1H-pyrrolo [2,3-b] pyridine-4-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3- b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.32 (t, J = 3.0 Hz, 1H), 7.10-6.96 ( m, 3H), 6.49 (s, 1H), 6.11 (s, 1H), 4.13 (d, J = 18.8 Hz, 1H), 3.80 (d, J = 4.3 Hz, 6H), 3.66 (dd, J = 12.9 , 4.2 Hz, 1H), 3.02 (s, 1H), 2.02 (dq, J = 8.6, 4.2, 3.3 Hz, 1H), 0.95-0.84 (m, 3H), 0.84-0.70 (m, 4H)

MS (ESI +) m / z 441 (M + H) ⁺

Example  329: N- (4- (1- (3,4- Dimethoxybenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3,4-dimethoxybenzoyl) -3-methyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.39 (t, J = 7.9 Hz, 1H), 7.32 (s, 1H), 7.07-6.96 (m, 3H), 6.49 (s, 1H), 4.17-3.99 (m, 2H), 3.80 (s, 3H), 3.62 (dd, J = 13.0, 4.1 Hz, 1H), 2.98 (s, 1H), 2.06-1.98 (m, 1H), 0.92 (s, 1H), 0.86-0.72 (m, 6H)

MS (ESI +) m / z 461 (M + H) ⁺

Example  330: N- (4- (1- (3- Methoxybenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-methoxybenzoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.39 (t, J = 7.9 Hz, 1H), 7.32 (s, 1H), 7.06-7.01 (m, 2H), 6.99 (d, J = 4.8 Hz, 1H), 6.49 (s, 1H), 4.19-4.00 (m, 2H), 3.80 (s, 3H), 3.62 (dd , J = 13.0, 4.1 Hz, 1H), 2.98 (s, 1H), 2.02 (td, J = 7.7, 3.9 Hz, 1H), 0.92 (s, 1H), 0.86-0.74 (m, 6H)

MS (ESI +) m / z 431 (M + H) ⁺

Example  331: N- (4- (3- methyl -1- (4- Nitrobenzoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (4-nitrobenzoyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.32 (dd, J = 8.5, 6.1 Hz, 3H), 7.84 (d, J = 9.3 Hz, 1H), 7.75 (d, J = 8.1 Hz, 2H), 7.32 (d, J = 9.2 Hz, 1H), 6.50 (d, J = 17.8 Hz, 1H), 6.09 (d, J = 79.2 Hz, 1H) , 4.37 (dd, J = 155.6, 19.8 Hz, 1H), 4.13-3.94 (m, 2H), 3.62 (d, J = 11.6 Hz, 1H), 3.04 (d, J = 44.3 Hz, 1H), 2.02 ( dq, J = 8.0, 3.9, 2.8 Hz, 1H), 0.95 (d, J = 6.8 Hz, 1H), 0.83-0.74 (m, 6H)

MS (ESI +) m / z 446 (M + H) ⁺

Example  332: N- (4- (1- (3- Acetylbenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-acetylbenzoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.55 (s, 1H), 8.08-8.03 (m, 1H), 8.01 (s, 1H), 7.84 (s, 1H), 7.74 (d, J = 7.5 Hz, 1H), 7.64 (t, J = 7.8 Hz, 1H), 7.32 (s, 1H), 6.50 (s, 1H), 6.10 (d, J = 74.1 Hz, 1H), 4.65-4.15 (m, 1H), 4.08 (d, J = 33.0 Hz, 1H), 3.64 (d, J = 13.1 Hz, 1H), 3.03 (d, J = 33.6 Hz, 1H), 2.63 (d, J = 1.4 Hz, 3H), 2.02 (dd, J = 8.6, 4.2 Hz, 1H), 0.95 (s, 1H), 0.85-0.73 (m, 6H)

MS (ESI +) m / z 443 (M + H) ⁺

Example  333: N- (4- (1- (4- Chlorobenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (4-chlorobenzoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.53 (t, J = 9.6 Hz, 4H), 7.32 (s, 1H), 6.50 (s, 1H), 6.09 (d, J = 63.6 Hz, 1H), 4.52 (d, J = 19.2 Hz, 1H), 4.10 (s, 1H), 3.63 (dd, J = 13.0, 4.2 Hz, 1H), 3.00 (s, 1H), 2.06-1.97 (m, 1H), 0.92 (s, 1H), 0.82-0.75 (m, 6H)

MS (ESI +) m / z 435, 437 (M + H) ⁺

Example  334: N- (4- (1- (3- Bromobenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-bromobenzoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.68 (d, J = 11.0 Hz, 2H), 7.45 (d, J = 8.0 Hz, 2H), 7.32 (s, 1H), 6.50 (s, 1H), 6.09 (d, J = 61.5 Hz, 1H), 4.55 (d, J = 19.7 Hz, 1H), 4.09 (s, 1H), 3.68-3.55 (m, 1H), 3.01 (d, J = 23.9 Hz, 1H), 2.02 (s, 1H), 0.93 (s, 1H), 0.84-0.74 (m, 6H)

MS (ESI +) m / z 479, 481 (M + H) ⁺

Example  335: N- (4- (1- (6- Chloronicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (6-chloronicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.55 (s, 1H), 8.59-8.51 (m, 1H), 7.99 (d, J = 8.0 Hz, 1H), 7.83 ( s, 1H), 7.64 (d, J = 8.2 Hz, 1H), 7.32 (s, 1H), 6.50 (d, J = 13.3 Hz, 1H), 6.08 (d, J = 69.0 Hz, 1H), 4.57- 4.17 (m, 1H), 4.14 (s, 1H), 3.65 (d, J = 12.5 Hz, 1H), 3.02 (s, 1H), 2.02 (dq, J = 8.1, 3.9, 2.8 Hz, 1H), 0.93 (s, 1H), 0.85-0.75 (m, 6H)

MS (ESI +) m / z 436, 438 (M + H) ⁺

Example  336: N- (4- (1- Isicotinoyl -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-isonicotinoyl-3-methyl-1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.74-8.64 (m, 2H), 7.83 (d, J = 10.7 Hz, 1H), 7.48- 7.44 (m, 2H), 7.32 (dt, J = 10.4, 2.9 Hz, 1H), 6.56-6.44 (m, 1H), 6.22-5.96 (m, 1H), 4.35 (dd, J = 166.5, 19.8 Hz, 1H), 4.06 (d, J = 9.2 Hz, 1H), 3.60 (dd, J = 13.4, 5.2 Hz, 1H), 3.02 (d, J = 39.5 Hz, 1H), 2.01 (td, J = 7.8, 7.4 , 3.7 Hz, 1H), 0.94 (d, J = 6.8 Hz, 1H), 0.84-0.74 (m, 6H)

MS (ESI +) m / z 402 (M + H) ⁺

Example  337: N- (4- (1- (6- Bromopicolinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (6-bromopicolinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 7.94-7.89 (m, 1H), 7.85 (d, J = 6.6 Hz, 1H), 7.78 ( dd, J = 8.1, 1.0 Hz, 1H), 7.69 (dd, J = 7.5, 3.8 Hz, 1H), 7.32 (dt, J = 10.3, 2.9 Hz, 1H), 6.49 (ddd, J = 8.0, 3.5, 1.9 Hz, 1H), 6.11 (dt, J = 60.3, 3.4 Hz, 1H), 4.61-4.17 (m, 1H), 4.16-4.11 (m, 1H), 3.63 (dd, J = 13.1, 3.5 Hz, 1H ), 3.52 (dd, J = 13.3, 4.1 Hz, 1H), 3.04 (d, J = 32.1 Hz, 1H), 2.05-1.99 (m, 1H), 0.90 (dd, J = 35.3, 6.8 Hz, 3H) , 0.83-0.72 (m, 4H)

MS (ESI +) m / z 480, 482 (M + H) ⁺

Example  338: N- (4- (1- (3- Bromobutanoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-bromobutanoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.55 (s, 1H), 7.83 (s, 1H), 7.32 (t, J = 2.9 Hz, 1H), 6.49 (s, 1H), 6.11 (s, 1H), 5.25 (s, 1H), 5.05 (s, 1H), 2.97 (s, 1H), 2.02 (s, 1H), 1.91 (s, 3H), 0.90-0.84 (m , 4H), 0.83-0.74 (m, 6H)

MS (ESI +) m / z 445, 447 (M + H) ⁺

Example  339: (E) -N- (4- (1- (5- Bromopent -2- Enoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((E) -N- (4- (1- (5-bromopent-2-enoyl) Synthesis of -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 457, 459 (M + H) ⁺

Example  340: N- (4- (1- (2- Cyclopentylacetyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyclopentylacetyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.53 (s, 1H), 7.83 (d, J = 3.8 Hz, 1H), 7.32 (s, 1H), 6.48 (dd, J = 3.5, 1.8 Hz, 1H), 6.10 (d, J = 12.7 Hz, 1H), 4.36 (t, J = 17.9 Hz, 1H), 3.96-3.87 (m, 1H), 2.96 (d, J = 19.7 Hz, 1H), 2.02 (d, J = 5.6 Hz, 1H), 1.78 (d, J = 7.5 Hz, 2H), 1.59 (s, 2H), 1.50 (d, J = 7.3 Hz, 2H), 1.15 ( s, 2H), 0.89 (d, J = 6.8 Hz, 2H), 0.84-0.77 (m, 7H)

MS (ESI +) m / z 407 (M + H) ⁺

Example  341: N- (4- (1- (2- (4- Methoxyphenyl ) Acetyl) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2- (4-methoxyphenyl) acetyl) -3- Synthesis of methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 445 (M + H) ⁺

Example  342: N- (4- (3- methyl -1- (3- Methylthiophene -2-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (3-methylthiophene-2-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.59 (d, J = 5.0 Hz, 1H), 7.32 (d, J = 2.9 Hz, 1H), 6.96 (s, 1H), 6.47 (dd, J = 3.5, 1.8 Hz, 1H), 6.12 (s, 1H), 4.08 (d, J = 18.8 Hz, 2H), 2.01 ( s, 1H), 0.86 (d, J = 6.9 Hz, 6H), 0.81-0.78 (m, 4H)

MS (ESI +) m / z 421 (M + H) ⁺

Example  343: N- (4- (3- methyl -One-( Pyrazine -2-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (pyrazine-2-carbonyl) -1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 8.90 (dd, J = 6.0, 1.6 Hz, 1H), 8.77 (d, J = 2.5 Hz, 1H), 8.74-8.70 (m, 1H), 7.83 (d, J = 10.3 Hz, 1H), 7.32 (dt, J = 8.9, 3.0 Hz, 1H), 6.49 (ddd, J = 9.7, 3.5, 1.8 Hz , 1H), 6.21-5.96 (m, 1H), 4.31-4.11 (m, 2H), 2.01 (s, 1H), 0.95 (d, J = 6.8 Hz, 2H), 0.82-0.74 (m, 7H)

MS (ESI +) m / z 403 (M + H) ⁺

Example  344: N- (4- (3- methyl -1- (5- Methylpyrazine -2-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (5-methylpyrazine-2-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 8.76 (d, J = 7.1 Hz, 1H), 8.61 (s, 1H), 7.83 (d, J = 9.7 Hz, 1H), 7.36-7.29 (m, 1H), 6.48 (d, J = 9.3 Hz, 1H), 6.10 (d, J = 72.7 Hz, 1H), 4.23-4.10 (m, 2H), 2.01 (s, 1H), 1.23 (s, 3H), 0.81-0.77 (m, 7H)

MS (ESI +) m / z 417 (M + H) ⁺

Example  345: N- (4- (3- methyl -1- (2- (thiophen-2-yl) acetyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (2- (thiophen-2-yl ) acetyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.53 (s, 1H), 7.82 (d, J = 7.2 Hz, 1H), 7.35 (dd, J = 26.6, 4.3 Hz, 3H), 7.00-6.93 (m, 3H), 6.45 (s, 1H), 6.09 (d, J = 15.0 Hz, 1H), 4.52-4.16 (m, 2H), 4.04 (dd, J = 17.1, 3.4 Hz , 2H), 2.95 (d, J = 8.0 Hz, 1H), 2.01 (s, 1H), 0.84 (d, J = 6.9 Hz, 3H), 0.81-0.77 (m, 4H)

MS (ESI +) m / z 421 (M + H) ⁺

Example  346: N- (4- (1- (2- (3- Fluorophenyl ) Acetyl) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2- (3-fluorophenyl) acetyl) -3- Synthesis of methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.53 (s, 1H), 7.82 (d, J = 5.9 Hz, 1H), 7.36 (dd, J = 6.4, 2.8 Hz, 1H), 7.33-7.31 (m, 1H), 7.13 (d, J = 9.0 Hz, 1H), 7.10-7.03 (m, 2H), 6.44 (p, J = 2.1 Hz, 1H), 6.09 (dd, J = 18.3, 3.5 Hz, 1H), 4.37 (dd, J = 28.8, 18.3 Hz, 1H), 4.12 (dd, J = 11.4, 6.1 Hz, 1H), 3.85 (d, J = 13.5 Hz, 2H), 3.71 (s, 2H), 2.04-1.98 (m, 1H), 0.83 (dd, J = 6.9, 2.0 Hz, 3H), 0.80-0.74 (m, 4H)

MS (ESI +) m / z 433 (M + H) ⁺

Example  347: N- (4- (1- (2- (3- Bromophenyl ) Acetyl) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (2- (3-bromophenyl) acetyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 8.12 (d, J = 6.2 Hz, 1H), 7.83 (d, J = 6.5 Hz, 1H) , 7.49 (d, J = 15.6 Hz, 1H), 7.44 (dt, J = 6.6, 3.1 Hz, 1H), 7.28 (s, 1H), 6.74-6.68 (m, 1H), 6.47-6.41 (m, 1H ), 6.09 (dt, J = 15.0, 3.4 Hz, 1H), 4.08 (d, J = 50.7 Hz, 2H), 3.84 (d, J = 15.6 Hz, 2H), 3.71 (s, 2H), 2.96 (s , 1H), 2.01 (t, J = 4.9 Hz, 1H), 0.84 (d, J = 6.8 Hz, 3H), 0.81-0.76 (m, 4H)

MS (ESI +) m / z 494 (M + H) ⁺

Example  348: N- (4- (1- (2- Chloroacetyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (2-chloroacetyl) -3-methyl-1,2, Synthesis of 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (d, J = 7.2 Hz, 1H), 7.32 (t, J = 3.0 Hz, 1H) , 6.48 (d, J = 3.1 Hz, 1H), 6.10 (d, J = 13.3 Hz, 1H), 4.52-4.41 (m, 2H), 4.37-4.04 (m, 2H), 2.97 (s, 1H), 2.00 (q, J = 7.3, 6.1 Hz, 1H), 0.88 (dd, J = 17.0, 6.9 Hz, 3H), 0.79 (dd, J = 9.1, 6.0 Hz, 4H)

MS (ESI +) m / z 373, 375 (M + H) ⁺

Example  349: N- (4- (1- (2- Chloronicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (2-chloronicotinoyl) -3-methyl-1,2, Synthesis of 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 436, 438 (M + H) ⁺

Example  350: N- (4- (1- (4- Hydroxybenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (4-hydroxybenzoyl) -3-methyl-1,2, Synthesis of 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 417 (M + H) ⁺

Example  351: N- (4- (1- (3,5- Dichloro -2- Hydroxybenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (3,5-dichloro-2-hydroxybenzoyl) -3- Synthesis of methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 486 (M + H) ⁺

Example  352: N- (4- (1- ( Benzofuran -2- Carbonyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (benzofuran-2-carbonyl) -3-methyl-1, 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 441 (M + H) ⁺

Example  353: N- (4- (1- (3,4- Dichlorobenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (3,4-dichlorobenzoyl) -3-methyl-1, 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 469, 471, 473 (M + H) ⁺

Example  354: N- (4- (3- methyl -1- (4- ( Methylsulfonyl ) Benzoyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane Carboxamide  N- (4- (3-methyl-1- (4- (methylsulfonyl) benzoyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6- yl) cyclopropanecarboxamide)

MS (ESI +) m / z 479 (M + H) ⁺

Example  355: N- (4- (1- (2- Chloro -4- Fluorobenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (2-chloro-4-fluorobenzoyl) -3-methyl- 1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 453, 455 (M + H) ⁺

Example  356: N- (4- (1- (2,4- Dimethoxybenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (2,4-dimethoxybenzoyl) -3-methyl-1, 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 461 (M + H) ⁺

Example  357: N- (4- (3- methyl -1- (2- ( Methylthio ) Benzoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (2- (methylthio) benzoyl)- 1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 447 (M + H) ⁺

Example  358: N- (4- (1- (3,5- Difluorobenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide N- (4- (1- (3,5-difluorobenzoyl) -3-methyl-1, 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 437 (M + H) ⁺

Example  359: N- (4- (1- (2-cyano-3- (4-fluorophenyl) propanoyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyano-3- (4-fluorophenyl) propanoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 472 (M + H) ⁺

Example  360: N- (4- (1- (2- Cyano -3- Phenylpropanoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyano-3-phenylpropanoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 454 (M + H) ⁺

Example  361: N- (4- (1- (1- Cyanocyclopentane -One- Carbonyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1-cyanocyclopentane-1-carbonyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 418 (M + H) ⁺

Example  362: N- (4- (3- methyl -1- (3- Morpholino -3- Oxopropanoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (3-morpholino-3-oxopropanoyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 452 (M + H) ⁺

Example  363: N- (4- (1- (2- Cyanoacetyl )-2- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -2-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 364 (M + H) ⁺

Example  364: N- (4- (3- methyl -1- (1H-pyrrole-2-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (1H-pyrrole-2-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 390 (M + H) ⁺

Example  365: N- (4- (3- methyl -1- (2- Phenylacetyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (2-phenylacetyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (s, 1H), 10.53 (s, 1H), 7.82 (d, J = 8.0 Hz, 1H), 7.33-7.23 (m, 6H), 6.41 ( d, J = 3.8 Hz, 1H), 6.07 (d, J = 23.4 Hz, 1H), 4.37 (dd, J = 29.9, 18.8 Hz, 1H), 4.13-4.01 (m, 1H), 3.81 (dd, J = 11.9, 4.6 Hz, 2H), 2.88 (s, 1H), 2.08 (d, J = 1.5 Hz, 2H), 2.01 (d, J = 1.5 Hz, 1H), 0.86-0.77 (m, 7H)

MS (ESI +) m / z 415 (M + H) ⁺

Example  366: N- (4- (9- (2- Fluoroisonicotinoyl ) -9- Azabicyclo [3.3.1] non -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (9- (2-fluoroisonicotinoyl) -9-azabicyclo [3.3.1] non-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.55 (d, J = 3.3 Hz, 1H), 8.35 (t, J = 5.6 Hz, 1H), 7.90 (d, J = 3.2 Hz, 1H), 7.47-7.38 (m, 1H), 7.37-7.25 (m, 2H), 6.53 (ddd, J = 33.6, 3.5, 1.8 Hz, 1H), 6.30 (dd, J = 68.3, 5.4 Hz , 1H), 5.34-4.94 (m, 1H), 4.31-3.88 (m, 1H), 2.96 (dd, J = 17.4, 8.2 Hz, 1H), 2.37 (d, J = 17.9 Hz, 1H), 2.02 ( s, 1H), 1.86-1.54 (m, 6H), 0.89 -0.71 (m, 4H)

MS (ESI +) m / z 446 (M + H) ⁺

Example  367: N- (4- (9- (2- Chloroisonicotinoyl ) -9- Azabicyclo [3.3.1] non 2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (9- (2-chloroisonicotinoyl) -9-azabicyclo [3.3.1] non-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.66-10.23 (m, 1H), 8.52 (dd, J = 7.0, 5.0 Hz, 1H), 7.90 (d, J = 3.4 Hz, 1H), 7.62 (d, J = 24.1 Hz, 1H), 7.54-7.42 (m, 1H), 7.35 (dt, J = 6.7, 2.9 Hz, 1H), 6.53 (ddd, J = 31.9, 3.6, 1.9 Hz, 1H), 6.31 (dd, J = 63.6, 5.4 Hz, 1H), 5.36-4.91 (m, 1H), 4.33-3.82 (m, 1H), 2.97 (dt, J = 17.0, 7.9 Hz, 1H ), 2.37 (d, J = 18.0 Hz, 1H), 2.01 (d, J = 8.1 Hz, 1H), 1.89-1.55 (m, 6H), 0.86-0.72 (m, 4H)

MS (ESI +) m / z 462, 464 (M + H) ⁺

Example  368: N- (4- (9- (6- Chloronicotinoyl ) -9- Azabicyclo [3.3.1] non -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (9- (6-chloronicotinoyl) -9-azabicyclo [3.3.1] non-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.55 (s, 1H), 8.53 (dd, J = 12.8, 2.3 Hz, 1H), 7.97 (ddd, J = 16.5, 8.3 , 2.4 Hz, 1H), 7.90 (s, 1H), 7.62 (t, J = 8.2 Hz, 1H), 7.35 (dt, J = 8.3, 2.8 Hz, 1H), 6.61-6.47 (m, 1H), 6.31 (dd, J = 63.7, 5.4 Hz, 1H), 5.35-4.89 (m, 1H), 4.23 (d, J = 141.9 Hz, 1H), 2.99 (dd, J = 18.2, 7.2 Hz, 1H), 2.38 ( d, J = 17.9 Hz, 1H), 2.08-1.97 (m, 1H), 1.87-1.57 (m, 6H), 0.85-0.71 (m, 4H)

MS (ESI +) m / z 462, 464 (M + H) ⁺

Example  369: N- (4- (9- (3- Fluoroisonicotinoyl ) -9- Azabicyclo [3.3.1] non -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (9- (3-fluoroisonicotinoyl) -9-azabicyclo [3.3.1] non-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (s, 1H), 10.56 (s, 1H), 8.72 (d, J = 2.5 Hz, 1H), 8.54 (dt, J = 4.4, 2.1 Hz, 1H), 7.90 (d, J = 7.1 Hz, 1H), 7.58 (t, J = 5.3 Hz, 1H), 7.36 (dt, J = 8.5, 3.0 Hz, 1H), 6.51 (ddd, J = 30.4, 3.6 , 1.9 Hz, 1H), 6.31 (dd, J = 71.8, 5.5 Hz, 1H), 5.20 (d, J = 113.1 Hz, 1H), 4.04 (d, J = 127.2 Hz, 1H), 2.92 (td, J = 21.1, 18.1, 6.8 Hz, 1H), 2.39 (d, J = 17.9 Hz, 1H), 2.02 (d, J = 7.6 Hz, 1H), 1.86 (d, J = 10.6 Hz, 2H), 1.74 (d , J = 34.5 Hz, 3H), 1.62 (d, J = 12.4 Hz, 1H), 0.86-0.72 (m, 4H)

MS (ESI +) m / z 446 (M + H) ⁺

Example  370: N- (4- (9- (4- Nitrobenzoyl ) -9- Azabicyclo [3.3.1] non -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (9- (4-nitrobenzoyl) -9-azabicyclo [3.3.1] non-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 8.31 (dd, J = 8.4, 5.7 Hz, 2H), 7.91 (d, J = 2.6 Hz, 1H), 7.73 (dd, J = 14.0, 8.4 Hz, 2H), 7.36 (dt, J = 10.5, 3.0 Hz, 1H), 6.61-6.47 (m, 1H), 6.31 (dd, J = 82.6, 5.4 Hz , 1H), 5.16 (d, J = 118.0 Hz, 1H), 4.13 (d, J = 138.3 Hz, 1H), 2.97 (ddd, J = 25.3, 18.1, 7.3 Hz, 1H), 2.38 (d, J = 17.9 Hz, 1H), 2.01 (d, J = 14.0 Hz, 1H), 1.81 (d, J = 30.8 Hz, 3H), 1.64 (d, J = 22.4 Hz, 3H), 0.83-0.74 (m, 4H)

MS (ESI +) m / z 472 (M + H) ⁺

Example  371: N- (4- (9- (3- Bromobenzoyl ) -9- Azabicyclo [3.3.1] non -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (9- (3-bromobenzoyl) -9-azabicyclo [3.3.1] non-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.55 (s, 1H), 7.90 (s, 1H), 7.68 (d, J = 7.1 Hz, 1H), 7.63 (d, J = 15.3 Hz, 1H), 7.50-7.39 (m, 2H), 7.36 (dd, J = 7.1, 3.9 Hz, 1H), 6.59-6.46 (m, 1H), 6.32 (dd, J = 60.3, 5.3 Hz , 1H), 5.12 (d, J = 114.0 Hz, 1H), 4.20 (d, J = 137.6 Hz, 1H), 3.03-2.84 (m, 1H), 2.45-2.33 (m, 1H), 2.02 (s, 1H), 1.83 (s, 3H), 1.71 (d, J = 24.0 Hz, 2H), 1.61 (d, J = 9.5 Hz, 1H), 0.85-0.73 (m, 4H)

MS (ESI +) m / z 506 (M + H) ⁺

Example  372: N- (4- (1- (2,6- Dichloroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2,6-dichloroisonicotinoyl) -3-methyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (d, J = 13.7 Hz, 1H), 7.72 (d, J = 6.8 Hz, 2H) , 7.36-7.29 (m, 1H), 6.49 (d, J = 9.7 Hz, 1H), 6.07 (d, J = 65.0 Hz, 1H), 4.50 (d, J = 19.2 Hz, 1H), 4.17-4.01 ( m, 3H), 2.01 (s, 1H), 1.23 (s, 3H), 0.80 (d, J = 7.3 Hz, 4H)

MS (ESI +) m / z 471 (M + H) ⁺

Example  373: N- (4- (1- (2,5- Dichloroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2,5-dichloroisonicotinoyl) -3-methyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.54 (s, 1H), 8.65 (s, 1H), 7.86 (d, J = 5.7 Hz, 1H), 7.81-7.75 ( m, 1H), 7.35-7.28 (m, 1H), 6.48 (d, J = 19.5 Hz, 1H), 6.08 (d, J = 63.9 Hz, 1H), 4.62-4.09 (m, 1H), 3.92 (d , J = 32.5 Hz, 1H), 2.02 (d, J = 7.1 Hz, 1H), 0.97 (s, 2H), 0.83-0.74 (m, 7H)

MS (ESI +) m / z 471 (M + H) ⁺

Example  374: N- (4- (1- (3,5- Dichloroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3,5-dichloroisonicotinoyl) -3-methyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.78 (d, J = 4.8 Hz, 2H), 7.83 (d, J = 15.9 Hz, 1H) , 7.33 (s, 1H), 6.46 (d, J = 11.8 Hz, 1H), 6.09 (d, J = 71.5 Hz, 1H), 4.30-4.19 (m, 1H), 2.01 (s, 2H), 0.99 ( d, J = 6.9 Hz, 2H), 0.87-0.71 (m, 7H)

MS (ESI +) m / z 470, 472, 474 (M + H) ⁺

Example  375: N- (4- (1- (2- Chloro -6- Methylisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-chloro-6-methylisonicotinoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (d, J = 12.0 Hz, 1H), 7.41 (d, J = 8.0 Hz, 1H) , 7.35 (d, J = 10.1 Hz, 1H), 7.31 (t, J = 3.6 Hz, 1H), 6.50 (dd, J = 10.5, 2.8 Hz, 1H), 6.08 (d, J = 65.0 Hz, 1H) , 4.32 (dd, J = 170.8, 19.5 Hz, 1H), 4.05 (s, 1H), 3.59 (d, J = 10.5 Hz, 1H), 2.96 (s, 1H), 2.03-1.97 (m, 1H), 0.94 (d, J = 6.8 Hz, 2H), 0.85-0.70 (m, 7H)

MS (ESI +) m / z 450, 452 (M + H) ⁺

Example  376: N- (4- (1- (3- Chloroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-chloroisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.54 (s, 1H), 8.77 (s, 1H), 8.64 (d, J = 5.1 Hz, 1H), 7.83 (d, J = 16.8 Hz, 1H), 7.53 (d, J = 4.7 Hz, 1H), 7.35-7.30 (m, 1H), 6.47 (d, J = 13.2 Hz, 1H), 6.09 (d, J = 68.6 Hz, 1H), 4.37 (d, J = 21.7 Hz, 1H), 3.91 (s, 1H), 2.01 (s, 1H), 0.98 (s, 2H), 0.88-0.74 (m, 7H)

MS (ESI +) m / z 436, 438 (M + H) ⁺

Example  377: N- (4- (1- (3- Hydroxyisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-hydroxyisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (d, J = 5.8 Hz, 1H), 8.26 (s, 1H), 8.11 (d, J = 4.8 Hz, 1H) , 7.80 (s, 1H), 7.21 (t, J = 3.6 Hz, 1H), 6.48 (s, 1H), 6.03 (d, J = 21.4 Hz, 1H), 5.81 (d, J = 7.7 Hz, 1H) , 4.53 (d, J = 19.6 Hz, 1H), 3.93 (s, 1H), 2.96 (s, 2H), 2.01 (s, 1H), 1.00-0.90 (m, 3H), 0.76 (d, J = 6.4 Hz, 4H)

MS (ESI +) m / z 418 (M + H) ⁺

Example  378: N- (4- (1- (2,3- Difluorobenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2,3-difluorobenzoyl) -3-methyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.20-8.09 (m, 1H), 7.83 (d, J = 14.1 Hz, 1H), 7.52 ( d, J = 4.4 Hz, 1H), 7.33 (q, J = 5.2, 4.0 Hz, 1H), 6.48 (d, J = 8.4 Hz, 1H), 6.07 (d, J = 75.5 Hz, 1H), 4.63- 4.19 (m, 1H), 4.15 (s, 1H), 4.04 (d, J = 7.8 Hz, 1H), 2.93 (s, 1H), 2.01 (s, 1H), 0.95-0.77 (m, 7H)

MS (ESI +) m / z 437 (M + H) ⁺

Example  379: N- (4- (3- methyl -1- (2- Methylisonicotinoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-methyl-1- (2-methylisonicotinoyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 10.1 Hz, 1H) , 7.31 (d, J = 8.6 Hz, 2H), 7.24 (s, 1H), 6.49 (d, J = 14.8 Hz, 1H), 6.08 (d, J = 70.1 Hz, 1H), 4.33 (dd, J = 173.7, 19.7 Hz, 1H), 4.04 (s, 1H), 2.52 (s, 3H), 2.01 (s, 1H), 0.94-0.77 (m, 7H)

MS (ESI +) m / z 416 (M + H) ⁺

Example  380: N- (4- (1- (6- Methoxynicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (6-methoxynicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 8.32-8.24 (m, 1H), 7.82 (d, J = 11.3 Hz, 1H), 7.32 ( d, J = 8.5 Hz, 1H), 7.03 (d, J = 5.2 Hz, 1H), 6.86 (s, 1H), 6.49 (d, J = 13.4 Hz, 1H), 6.08 (d, J = 67.4 Hz, 1H), 4.58-4.08 (m, 1H), 4.04 (s, 1H), 3.89 (s, 3H), 3.59 (d, J = 13.6 Hz, 2H), 2.95 (s, 1H), 2.01 (s, 1H ), 0.94-0.77 (m, 7H)

MS (ESI +) m / z 432 (M + H) ⁺

Example  381: N- (4- (1- (2- Aminoisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-aminoisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 417 (M + H) ⁺

Example  382: N- (4- (1- (2- Bromoisononitinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-bromoisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 8.51 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 12.2 Hz, 1H) , 7.76 (d, J = 8.0 Hz, 1H), 7.59-7.48 (m, 1H), 7.33 (dd, J = 7.4, 4.4 Hz, 1H), 6.55-6.41 (m, 1H), 6.08 (d, J = 65.3 Hz, 1H), 4.33 (dd, J = 166.6, 19.5 Hz, 1H), 4.05 (d, J = 3.5 Hz, 1H), 3.59 (dd, J = 13.2, 4.2 Hz, 1H), 3.02 (d , J = 40.4 Hz, 1H), 2.00 (dt, J = 7.9, 4.7 Hz, 1H), 0.95-0.77 (m, 7H)

MS (ESI +) m / z 481 (M + H) ⁺

Example  383: N- (4- (1- (2- Hydroxyisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-hydroxyisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 418 (M + H) ⁺

Example  384: N- (4- (3- methyl -1- (2- ( Trifluoromethyl ) Isicotinoyl ) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] cyclopropane Carboxamide  (N- (4- (3-methyl-1- (2- (trifluoromethyl) isonicotinoyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 8.90 (d, J = 4.9 Hz, 1H), 8.03-7.77 (m, 3H), 7.37- 7.26 (m, 1H), 6.50 (d, J = 12.5 Hz, 1H), 6.08 (d, J = 73.2 Hz, 1H), 4.62-4.13 (m, 1H), 4.07 (s, 1H), 2.98 (s , 1H), 2.07-1.96 (m, 1H), 0.97-0.77 (m, 7H)

MS (ESI +) m / z 470 (M + H) ⁺

Example  385: N- (4- (1- (2- Fluoroisonicotinoyl ) -2,2-dimethyl-1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-fluoroisonicotinoyl) -2,2-dimethyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 8.34 (d, J = 5.1 Hz, 1H), 7.90 (s, 1H), 7.43-7.33 ( m, 2H), 7.27 (d, J = 2.2 Hz, 1H), 6.54 (dd, J = 3.6, 1.9 Hz, 1H), 6.45 (t, J = 4.6 Hz, 1H), 3.95 (d, J = 4.5 Hz, 2H), 2.72 (s, 2H), 2.03 (hept, J = 4.7 Hz, 1H), 1.58 (s, 6H), 0.87-0.71 (m, 4H).

MS (ESI +) m / z 434 (M + H) ⁺

Example  386: N- (4- (1- (2- Chloroisonicotinoyl ) -2,2-dimethyl-1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-chloroisonicotinoyl) -2,2-dimethyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 8.57-8.44 (m, 1H), 7.90 (s, 1H), 7.59 (s, 1H), 7.45 (s, 1H), 7.35 (s, 1H), 6.49 (d, J = 35.6 Hz, 2H), 3.95 (s, 2H), 2.72 (s, 2H), 2.03 (s, 1H), 1.57 (d , J = 5.9 Hz, 6H), 0.83 (d, J = 20.3 Hz, 4H)

MS (ESI +) m / z 450, 452 (M + H) ⁺

Example  387: N- (4- (1- (2- Cyanoacetyl ) -2,2-dimethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -2,2-dimethyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.56 (s, 1H), 7.89 (s, 1H), 7.36 (t, J = 3.0 Hz, 1H), 6.54 (dd, J = 3.5, 1.8 Hz, 1H), 6.46 (t, J = 4.6 Hz, 1H), 4.09 (s, 2H), 4.02 (d, J = 4.6 Hz, 2H), 2.64 (s, 2H), 2.05- 1.98 (m, 1H), 1.47 (s, 6H), 0.85-0.71 (m, 4H)

MS (ESI +) m / z 378 (M + H) ⁺

Example  388: (R) -N- (4- (1- (2- Cyanoacetyl ) -6- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((R) -N- (4- (1- (2-cyanoacetyl) -6-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.53 (s, 1H), 7.85 (d, J = 3.4 Hz, 1H), 7.35 (t, J = 3.0 Hz, 1H) , 6.60-6.38 (m, 1H), 6.24 (dd, J = 24.2, 3.9 Hz, 1H), 4.99-4.41 (m, 1H), 4.59-3.69 (ddd, J = 13.8, 5.2 Hz, 1H), 4.14 (m, 1H), 3.04-2.75 (m, 1H), 2.46-2.31 (m, 1H), 2.08-1.93 (m, 1H), 1.31 (dd, J = 42.5, 6.8 Hz, 3H), 0.80 (m , 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  389: (R) -N- (4- (1- (2- Cyanoacetyl )-2- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((R) -N- (4- (1- (2-cyanoacetyl) -2-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.54 (s, 1H), 7.85 (s, 1H), 7.35 (t, J = 3.0 Hz, 1H), 6.53 (d, J = 3.0 Hz, 1H), 6.28 (d, J = 23.9 Hz, 1H), 5.02-4.88 (m, 1H), 4.66 (d, J = 20.0 Hz, 1H), 4.28-3.95 (m, 4H), 3.66 (d, J = 20.5 Hz, 1H), 3.01 (d, J = 17.1 Hz, 1H), 2.37-2.26 (m, 1H), 2.08-1.93 (m, 1H), 1.31-1.18 (m, 3H) , 0.82 (m, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  390: (S) -N- (4- (1- (2- Cyanoacetyl ) -6- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2-cyanoacetyl) -6-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.53 (s, 1H), 7.85 (d, J = 3.7 Hz, 1H), 7.35 (t, J = 3.0 Hz, 1H) , 6.53 (dd, J = 3.4, 1.7 Hz, 1H), 6.33-6.13 (m, 1H), 4.99 -4.40 (m, 1H), 4.56-3.71 (dd, J = 13.7, 5.2 Hz, 1H), 4.34 -3.97 (m, 2H), 3.39-3.23 (m, 1H), 2.87 (dt, J = 46.3, 13.5 Hz, 1H), 2.48-2.31 (m, 1H), 2.1-1.95 (m, 1H), 1.31 (dd, J = 42.6, 6.7 Hz, 3H)., 0.80 (dt, J = 11.5, 5.5 Hz, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example  391: (S) -N- (4- (1- (2- Cyanoacetyl )-2- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2-cyanoacetyl) -2-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.54 (s, 1H), 7.85 (s, 1H), 7.35 (t, J = 3.0 Hz, 1H), 6.53 (d, J = 3.0 Hz, 1H), 6.28 (d, J = 23.9 Hz, 1H), 5.02-4.88 (m, 1H), 4.66 (d, J = 20.0 Hz, 1H), 4.28-3.95 (m, 4H), 3.66 (d, J = 20.5 Hz, 1H), 3.01 (d, J = 17.1 Hz, 1H), 2.37-2.26 (m, 1H), 2.08-1.93 (m, 1H), 1.31-1.18 (m, 3H) , 0.82 (m, 4 H).

MS (ESI +) m / z 364 (M + H) ⁺

Example  392: N- (4- (1- (2- Cyanoisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoisonicotinoyl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.59 (d, J = 3.2 Hz, 1H), 8.87 (d, J = 5.4 Hz, 1H), 8.20 (d, J = 9.9 Hz, 1H), 7.83 (q, J = 4.9 Hz, 2H), 7.33 (d, J = 9.6 Hz, 1H), 6.50 (d, J = 15.1 Hz, 1H), 6.07 (d, J = 75.8 Hz , 1H), 4.59-4.15 (m, 1H), 4.06 (s, 1H), 3.58 (s, 1H), 3.26 (s, 1H), 3.03 (d, J = 43.5 Hz, 1H), 2.00 (s, 1H), 0.95-0.76 (m, 7H).

MS (ESI +) m / z 427 (M + H) ⁺

Example  393: N- (4- (1- (2- Cyanoacetyl )-2-( Trifluoromethyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -2- (trifluoromethyl) -1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 418 (M + H) ⁺

Example  394: N- (4- (9- (2- Cyanoacetyl ) -9- Azabicyclo [3.3.1] non 2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (9- (2-cyanoacetyl) -9-azabicyclo [3.3.1] non-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.55 (s, 1H), 7.89 (s, 1H), 7.35 (d, J = 3.2 Hz, 1H), 6.55 (d, J = 11.5 Hz, 1H), 6.29 (d, J = 13.7 Hz, 1H), 5.17 (s, 1H), 4.71 (d, J = 141.5 Hz, 1H), 4.22-4.11 (m, 2H), 3.18- 3.07 (m, 1H), 2.91-2.64 (m, 1H), 2.38 (d, J = 18.0 Hz, 2H), 2.02 (s, 1H), 1.80 (d, J = 8.8 Hz, 2H), 1.62 (d , J = 31.9 Hz, 2H), 0.79 (d, J = 11.9 Hz, 4H).

MS (ESI +) m / z 390 (M + H) ⁺

Example  395: (S) -N- (4- (1- (2- Fluoroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2-fluoroisonicotinoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 420 (M + H) ⁺

Example  396: (S) -N- (4- (1- (2,3- Difluoroisonicotinoyl ) -3- methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- Synthesis of (1- (2,3-difluoroisonicotinoyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.55 (s, 1H), 8.21-8.13 (m, 1H), 7.84 (d, J = 14.3 Hz, 1H), 7.58- 7.49 (m, 1H), 7.33 (dt, J = 5.5, 2.8 Hz, 1H), 6.48 (d, J = 8.5 Hz, 1H), 6.08 (dd, J = 75.5, 3.0 Hz, 1H), 4.63-4.22 (m, 1H), 4.18 (d, J = 18.5 Hz, 1H), 4.12-3.92 (m, 1H), 3.61 (dd, J = 30.9, 12.6 Hz, 1H), 3.01 (d, J = 64.9 Hz, 1H), 2.02 (s, 1H), 0.97-0.91 (m, 1H), 0.84-0.73 (m, 6H).

MS (ESI +) m / z 438 (M + H) ⁺

Example  397: (S) -N- (4- (1- (3- Bromobenzoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (3-bromobenzoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.83 (s, 1H), 7.67 (t, J = 8.0 Hz, 2H), 7.45 (d, J = 8.6 Hz, 2H), 7.32 (s, 1H), 6.50 (s, 1H), 6.21-5.96 (m, 1H), 4.59-4.12 (m, 1H), 4.09 (s, 1H), 3.61 (d , J = 12.3 Hz, 1H), 3.02 (d, J = 28.7 Hz, 1H), 2.01 (d, J = 7.7 Hz, 1H), 0.94-0.75 (m, 7H).

MS (ESI +) m / z 479, 481 (M + H) ⁺

Example  398: (S) -N- (4- (3- methyl -1- (4- Nitrobenzoyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (3-methyl-1- (4-nitrobenzoyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.33 (d, J = 8.0 Hz, 2H), 7.84 (d, J = 9.4 Hz, 1H) , 7.75 (d, J = 8.1 Hz, 2H), 7.33 (s, 1H), 6.50 (d, J = 17.6 Hz, 1H), 6.09 (d, J = 79.5 Hz, 1H), 4.37 (dd, J = 155.9, 19.7 Hz, 1H), 4.08 (d, J = 23.1 Hz, 1H), 3.61 (d, J = 13.3 Hz, 1H), 3.13-2.93 (m, 1H), 2.02 (s, 1H), 0.98- 0.90 (m, 1 H), 0.79 (t, J = 8.0 Hz, 6 H).

MS (ESI +) m / z 446 (M + H) ⁺

Example  399: (S) -N- (4- (1- (2- Chloroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2-chloroisonicotinoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.61-8.46 (m, 1H), 7.84 (d, J = 12.1 Hz, 1H), 7.65 ( d, J = 7.5 Hz, 1H), 7.50 (d, J = 5.6 Hz, 1H), 7.38-7.26 (m, 1H), 6.53-6.42 (m, 1H), 6.23-5.97 (m, 1H), 4.34 (dd, J = 164.5, 20.3 Hz, 1H), 4.05 (s, 1H), 3.63-3.53 (m, 1H), 3.12-2.93 (m, 1H), 2.01 (d, J = 7.4 Hz, 1H), 0.94 (d, J = 6.8 Hz, 1H), 0.84-0.74 (m, 6H).

MS (ESI +) m / z 436, 438 (M + H) ⁺

Example  400: (S) -N- (4- (1- (6- Chloronicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (6-chloronicotinoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.55 (s, 1H), 7.99 (d, J = 7.8 Hz, 1H), 7.84 (s, 1H), 7.64 (d, J = 8.2 Hz, 1H), 7.33 (d, J = 5.2 Hz, 1H), 6.50 (d, J = 13.3 Hz, 1H), 6.09 (d, J = 69.3 Hz, 1H) , 4.57-4.18 (m, 1H), 4.14 (s, 1H), 3.65 (d, J = 12.1 Hz, 1H), 3.05 (d, J = 23.3 Hz, 1H), 2.01 (d, J = 7.4 Hz, 1H), 0.94 (s, 1H), 0.83-0.74 (m, 6H).

MS (ESI +) m / z 436, 438 (M + H) ⁺

Example  401: (S) -N- (4- (1- (2- Chloroacetyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2-chloroacetyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 7.84 (d, J = 6.9 Hz, 1H), 7.33 (s, 1H), 6.48 (s, 1H), 6.10 (d, J = 14.2 Hz, 1H), 4.54-4.40 (m, 2H), 4.37-3.97 (m, 2H), 3.77-3.36 (m, 2H), 3.02 (d, J = 32.0 Hz , 1H), 2.01 (d, J = 7.2 Hz, 1H), 0.92-0.84 (m, 3H), 0.83-0.69 (m, 4H).

MS (ESI +) m / z 373, 375 (M + H) ⁺

Example  402: (S) -N- (4- (1- (3- Fluoroisonicotinoyl ) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (3-fluoroisonicotinoyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.74 (s, 1H), 8.64-8.50 (m, 1H), 7.84 (d, J = 14.3 Hz, 1H), 7.58 (d, J = 4.9 Hz, 1H), 7.33 (dd, J = 7.1, 3.4 Hz, 1H), 6.49 (d, J = 10.2 Hz, 1H), 6.09 (d, J = 71.2 Hz, 1H), 4.70-4.08 (m, 2H), 3.99 (s, 1H), 3.59 (t, J = 14.5 Hz, 1H), 3.12-2.90 (m, 1H), 2.02 (s, 1H), 0.95 (d, J = 6.9 Hz, 1H), 0.79 (q, J = 6.6 Hz, 6H).

MS (ESI +) m / z 420 (M + H) ⁺

Example  403: (S) -N- (4- (1- (2- Cyano -3- (thiophen-2-yl) acryloyl) -3- methyl -1,2,3,6-tetrahydropyridin-4-yl) -2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2 -cyano-3- (thiophen-2-yl) acryloyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 8.20-8.03 (m, 1H), 7.95 (s, 1H), 7.86 (q, J = 3.1 Hz, 1H), 7.57 (d, J = 6.6 Hz, 1H), 7.37-7.27 (m, 2H), 6.50 (s, 1H), 6.15 (d, J = 13.1 Hz, 1H), 4.45 (d, J = 18.5 Hz, 1H), 4.39-3.46 (m, 3H), 3.10 (s, 1H), 2.09-1.97 (m, 1H), 0.96-0.87 (m, 3H), 0.83-0.74 (m, 4H).

MS (ESI +) m / z 458 (M + H) ⁺

Example  404: (S) -N- (4- (1- (2- (cyanomethyl) -3-phenylacryloyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (S) -N- (4- (1- (2- (cyanomethyl) -3-phenylacryloyl) -3- Synthesis of methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.56 (s, 1H), 7.99-7.91 (m, 2H), 7.87 (d, J = 8.8 Hz, 1H), 7.58 ( d, J = 4.2 Hz, 2H), 7.50 (s, 1H), 7.34 (s, 1H), 6.51 (s, 1H), 6.13 (s, 1H), 4.47 (s, 1H), 4.37-4.07 (m , 1H), 3.97 (d, J = 22.1 Hz, 1H), 3.80-3.45 (m, 1H), 3.10 (s, 1H), 2.01 (d, J = 8.0 Hz, 1H), 0.92 (d, J = 7.1 Hz, 3H), 0.79 (t, J = 8.3 Hz, 4H).

MS (ESI +) m / z 466 (M + H) ⁺

Example  405: (S) -N- (4- (3-methyl-1- (1-methyl-2-oxo-1,2-dihydropyridine-3-carbonyl) -1,2,3,6-tetra Hydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (3-methyl-1- (1- methyl-2-oxo-1,2-dihydropyridine-3-carbonyl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.54 (s, 1H), 7.82 (d, J = 12.8 Hz, 2H), 7.51 (d, J = 6.6 Hz, 1H) , 7.32 (d, J = 6.5 Hz, 1H), 6.48 (s, 1H), 6.29 (d, J = 7.0 Hz, 1H), 6.08 (d, J = 54.1 Hz, 1H), 4.27 (dd, J = 137.1, 19.1 Hz, 2H), 4.00 (s, 1H), 3.56 (s, 1H), 3.49 (s, 3H), 2.98 (s, 1H), 2.02 (s, 1H), 0.94 (d, J = 6.9 Hz, 1H), 0.85-0.72 (m, 6H).

MS (ESI +) m / z 432 (M + H) ⁺

Example  406: (S) -N- (4- (1- (2- (1-cyanocyclohexyl) acetyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H -Pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2- (1-cyanocyclohexyl) acetyl) -3-methyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.84 (d, J = 7.1 Hz, 1H), 7.33 (s, 1H), 6.49 (s, 1H), 6.09 (d, J = 20.9 Hz, 1H), 4.43-4.27 (m, 1H), 4.13-3.93 (m, 1H), 3.72-3.51 (m, 1H), 3.38 (d, J = 12.6 Hz , 1H), 2.99 (d, J = 23.7 Hz, 1H), 2.84 (d, J = 9.4 Hz, 1H), 2.69 (d, J = 8.1 Hz, 1H), 2.09 (d, J = 13.0 Hz, 2H ), 2.01 (d, J = 7.2 Hz, 1H), 1.67 (d, J = 11.6 Hz, 3H), 1.54-1.33 (m, 4H), 1.18 (dd, J = 20.2, 9.7 Hz, 1H), 0.87 (dd, J = 17.1, 6.8 Hz, 3H), 0.83-0.71 (m, 4H).

MS (ESI +) m / z 446 (M + H) ⁺

Example  407: (S) -N- (4- (1- (4-cyanotetrahydro-2H-pyran-4-carbonyl) -3-methyl-1,2,3,6-tetrahydropyridine-4- Yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (4-cyanotetrahydro-2H-pyran-4-carbonyl ) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.84 (d, J = 6.7 Hz, 1H), 7.32 (t, J = 3.0 Hz, 1H) , 6.48 (dt, J = 4.7, 2.3 Hz, 1H), 6.09 (dt, J = 28.1, 3.4 Hz, 1H), 4.28 (dd, J = 52.8, 18.4 Hz, 1H), 4.07-3.96 (m, 1H ), 3.94-3.57 (m, 1H), 3.43 (ddd, J = 12.4, 7.9, 4.5 Hz, 1H), 3.00 (s, 1H), 2.90-2.62 (m, 2H), 2.01 (td, J = 7.4 , 3.7 Hz, 1H), 1.34-1.14 (m, 3H), 1.01-0.89 (m, 2H), 0.87 (dd, J = 6.9, 5.1 Hz, 3H), 0.84-0.73 (m, 4H).

MS (ESI +) m / z 434 (M + H) ⁺

Example  408: (S) -N- (4- (1- (2-cyano-3-methylbut-2-enoyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2-cyano-3-methylbut-2-enoyl) Synthesis of -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.56 (s, 1H), 7.84 (s, 1H), 7.33 (s, 1H), 6.48 (s, 1H), 6.11 ( d, J = 21.5 Hz, 1H), 4.58-4.23 (m, 1H), 4.07 (t, J = 22.3 Hz, 2H), 3.77-3.55 (m, 1H), 3.54-3.44 (m, 1H), 3.03 (s, 1H), 2.14 (s, 3H), 2.02 (s, 1H), 1.93 (d, J = 7.1 Hz, 3H), 0.88 (d, J = 6.7 Hz, 3H), 0.79 (dd, J = 13.1, 5.2 Hz, 4H).

MS (ESI +) m / z 404 (M + H) ⁺

Example  409: N- (4- (1- (2- Cyanoacetyl ) -2,6- Diethyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -2,6-diethyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.55 (s, 1H), 7.85 (s, 1H), 7.44-7.34 (m, 1H), 6.46 (dd, J = 3.8 , 1.8 Hz, 1H), 6.30 (t, J = 3.0 Hz, 1H), 4.70-4.55 (m, 1H), 4.29-4.01 (m, 2H), 3.90 (d, J = 6.7 Hz, 1H), 2.01 (d, J = 5.2 Hz, 1H), 1.65 (dddd, J = 51.1, 21.4, 14.7, 7.4 Hz, 4H), 1.23 (s, 2H), 1.08-0.97 (m, 3H), 0.88 (dt, J = 13.5, 7.3 Hz, 3H), 0.83-0.71 (m, 4H).

MS (ESI +) m / z 406 (M + H) ⁺

Example  410: N- (4- (1- (2- Cyanoacetyl ) -2-isopropyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -2-isopropyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.54 (s, 1H), 7.87 (s, 1H), 7.35 (s, 1H), 6.58-6.40 (m, 1H), 6.37-6.19 (m, 1H), 4.29-4.08 (m, 2H), 4.08-3.89 (m, 1H), 3.84-3.54 (m, 1H), 3.01-2.81 (m, 1H), 2.37 (s, 1H ), 2.01 (s, 2H), 1.23 (s, 2H), 1.06 (d, J = 6.6 Hz, 2H), 0.92 (t, J = 5.7 Hz, 2H), 0.87 (dd, J = 13.0, 6.5 Hz , 2H), 0.83-0.75 (m, 4H).

MS (ESI +) m / z 392 (M + H) ⁺

Example  411: N- (4- (1- (2- Cyanoacetyl ) -6-propyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -6-propyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 392 (M + H) ⁺

Example  412: N- (4- (6- ( tert -Butyl) -1- (2- Cyanoacetyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (6- (tert-butyl) -1- (2-cyanoacetyl)) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 406 (M + H) ⁺

Example  413: N- (4- (1- (2- Cyanoacetyl ) -2-ethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -2-ethyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.54 (s, 1H), 7.85 (s, 1H), 7.35 (t, J = 2.9 Hz, 1H), 6.52 (s, 1H), 6.25 (d, J = 28.2 Hz, 1H), 4.81-4.65 (m, 1H), 4.20-4.08 (m, 2H), 4.00-3.90 (m, 1H), 3.01 (d, J = 17.1 Hz , 1H), 2.08-1.91 (m, 1H), 1.74-1.46 (m, 2H), 1.23 (s, 2H), 0.86 (dd, J = 12.2, 7.3 Hz, 3H), 0.86-0.69 (m, 4H ).

MS (ESI +) m / z 378 (M + H) ⁺

Example  414: N- (4- (5- (2- Cyanoacetyl ) -5- Azaspiro [3.5] paddy field -7-en-8-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (5- (2-cyanoacetyl) -5-azaspiro Synthesis of [3.5] non-7-en-8-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.54 (s, 1H), 7.86 (s, 1H), 7.37-7.15 (m, 1H), 6.55 (s, 1H), 6.28 (s, 1H), 4.03 (s, 4H), 2.36 (s, 2H), 2.12-1.97 (m, 3H), 1.79 (dt, J = 28.8, 10.1 Hz, 2H), 0.83-0.74 (m, 4H).

MS (ESI +) m / z 390 (M + H) ⁺

Example  415: (S) -N- (4- (1- (2- (1-cyanocyclopropyl) acetyl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H -Pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (2- (1-cyanocyclopropyl) acetyl) -3-methyl-1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 404 (M + H) ⁺

Example  416: (R) -N- (4- (1- (2- Cyanoacetyl ) -6-ethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((R) -N- (4- (1- (2-cyanoacetyl) -6-ethyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 378 (M + H) ⁺

Example  417: (R) -N- (4- (1- (2- Cyanoacetyl ) -2-ethyl-1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((R) -N- (4- (1- (2-cyanoacetyl) -2-ethyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 378 (M + H) ⁺

Example  418: N- (4- (1- (3- Cyanopropanoyl ) -1,4,5,6- Tetrahydropyridine -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-cyanopropanoyl) -1,4,5,6 -tetrahydropyridin-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 364 (M + H) ⁺

Example  419: N- (4- (1- (2- Cyanoacetyl ) -1,4,5,6- Tetrahydropyridine -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -1,4,5,6 -tetrahydropyridin-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 350 (M + H) ⁺

Example  420: N- (4- (1- (2- Cyanoacetyl ) -1,2,5,6- Tetrahydropyridine -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -1,2,5,6 -tetrahydropyridin-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (s, 1H), 10.55 (d, J = 5.3 Hz, 1H), 7.84 (d, J = 7.8 Hz, 1H), 7.36 (q, J = 2.7 Hz, 1H), 6.60-6.50 (m, 1H), 6.48-6.33 (m, 1H), 4.35 (dd, J = 40.1, 2.7 Hz, 2H), 4.15 (d, J = 5.6 Hz, 2H), 3.61 (dt, J = 43.3, 5.8 Hz, 2H), 2.46-2.28 (m, 2H), 2.02 (d, J = 6.0 Hz, 1H), 0.90-0.71 (m, 4H).

MS (ESI +) m / z 350 (M + H) ⁺

Example  421: N- (4- (1- (3- Cyanopropanoyl ) -1,2,5,6- Tetrahydropyridine -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-cyanopropanoyl) -1,2,5,6 -tetrahydropyridin-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.55 (s, 1H), 7.86 (d, J = 4.1 Hz, 1H), 7.35 (t, J = 3.0 Hz, 1H) , 6.58-6.51 (m, 1H), 6.48-6.39 (m, 1H), 4.46-4.29 (m, 2H), 3.65 (dt, J = 24.4, 5.8 Hz, 2H), 2.82 (dt, J = 14.1, 6.8 Hz, 2H), 2.64 (dt, J = 14.0, 6.7 Hz, 2H), 2.38 (d, J = 39.9 Hz, 2H), 2.01 (d, J = 7.9 Hz, 1H), 0.85-0.76 (m, 4H).

MS (ESI +) m / z 364 (M + H) ⁺

Example  422: N- (4- (1- (2- Cyanoacetyl ) -2,5,6,7- Tetrahydro -1H- Azepine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -2,5,6,7 -tetrahydro-1H-azepin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (d, J = 7.3 Hz, 1H), 10.57-10.47 (m, 1H), 7.79 (d, J = 8.5 Hz, 1H), 7.32 (q, J = 3.0 Hz, 1H), 6.40 (ddd, J = 1.9, 3.6, 8.7 Hz, 1H), 6.24 (dt, J = 5.4, 32.4 Hz, 1H), 4.15 (dd, J = 5.4, 11.3 Hz, 2H ), 4.08 (d, J = 20.8 Hz, 2H), 3.67 (dt, J = 5.9, 41.9 Hz, 2H), 2.71 (dt, J = 5.7, 16.7 Hz, 2H), 2.01 (t, J = 5.9 Hz , 1H), 1.96 (s, 1H), 1.91 (d, J = 12.1 Hz, 1H), 0.84-0.75 (m, 4H).

MS (ESI +) m / z 364 (M + H) ⁺

Example  423: N- (4- (1- (2- Fluoroisonicotinoyl ) -2,5,6,7- Tetrahydro -1H-azin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-fluoroisonicotinoyl) -2, 5,6,7-tetrahydro-1H-azepin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 420 (M + H) ⁺

Example  424: N- (4- (1- (2,3- Difluoroisonicotinoyl ) -2,5,6,7- Tetrahydro -1H-azin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2,3-difluoroisonicotinoyl)- 2,5,6,7-tetrahydro-1H-azepin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 438 (M + H) ⁺

Example  425: N- (4- (1- (2- Cyanoacetyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -1,2,3, 6-tetrahydropyridin-4-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.95 (s, 1H), 10.44 (d, J = 5.0 Hz, 1H), 7.42 (s, 1H), 6.89 (d, J = 11.4 Hz, 1H) , 6.70 (s, 1H), 4.24 (d, J = 16.4 Hz, 2H), 4.14 (d, J = 17.7 Hz, 2H), 3.65 (dt, J = 5.8, 50.5 Hz, 2H), 2.85-2.62 ( m, 2H), 2.17 (s, 1H), 0.81-0.77 (m, 4H).

MS (ESI +) m / z 351 (M + H) ⁺

Example  426: N- (4- (1- (2- Cyanoacetyl ) -2,5- Dehydro -1H-pyrrole-3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoacetyl) -2,5-dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] Synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.57 (s, 1H), 10.61 (s, 1H), 7.85 (d, J = 3.2 Hz, 1H), 7.43 (s, 1H), 6.74 (d, J = 20.3 Hz, 2H), 4.75 (s, 1H), 4.55 (d, J = 16.5 Hz, 2H), 4.38 (s, 1H), 4.15 (d, J = 3.5 Hz, 1H), 4.04 (d, J = 3.2 Hz, 1H), 2.03 (s, 1H), 0.81 (s, 4H).

MS (ESI +) m / z 336 (M + H) ⁺

Example  427: N- (4- (1- (3- Cyanopropanoyl ) -2,5- Dehydro -1H-pyrrole-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-cyanopropanoyl) -2,5 -dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.56 (s, 1H), 10.60 (s, 1H), 7.86 (d, J = 5.1 Hz, 1H), 7.43 (d, J = 2.3 Hz, 1H) , 6.79-6.69 (m, 2H), 4.77 (s, 1H), 4.56 (s, 2H), 4.40-4.31 (m, 1H), 2.96 (s, 1H), 2.83 (t, J = 6.9 Hz, 1H ), 2.77-2.72 (m, 1H), 2.68 (q, J = 6.6 Hz, 2H), 2.02 (dd, J = 4.8, 9.6 Hz, 1H), 0.81 (dt, J = 4.0, 18.4 Hz, 4H) .

MS (ESI +) m / z 350 (M + H) ⁺

Example  428: N- (4- (1- (3,3,3- Trifluoropropanoyl ) -2,5- Dehydro -1H-pyrrole-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3,3,3-trifluoropropanoyl) -2,5-dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.56 (s, 1H), 10.60 (d, J = 2.7 Hz, 1H), 7.86 (d, J = 2.8 Hz, 1H), 7.43 (d, J = 3.1 Hz, 1H), 6.81-6.63 (m, 2H), 4.80 (d, J = 4.2 Hz, 1H), 4.58 (s, 2H), 4.38 (d, J = 4.0 Hz, 1H), 3.72 (dq, J = 11.0, 41.9 Hz, 2H), 2.02 (q, J = 3.0, 4.8 Hz, 1H), 0.87-0.74 (m, 4H).

MS (ESI +) m / z 379 (M + H) ⁺

Example  429: N- (4- (1- (4,4,4- Trifluorobutanoyl ) -2,5- Dehydro -1H-pyrrole-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (4,4,4-trifluorobutanoyl) -2,5-dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.62 (s, 1H), 7.87 (s, 1H), 7.43 (s, 1H), 6.74 (t, J = 11.6 Hz, 2H), 4.80 (s, 1H), 4.57 (d, J = 10.9 Hz, 2H), 4.37 (s, 1H), 2.74-2.61 (m, 2H), 2.04-1.98 (m, 1H), 1.15 (s , 2H), 0.82 (dd, J = 6.5, 21.7 Hz, 4H).

MS (ESI +) m / z 393 (M + H) ⁺

Example  430: N- (4- (1- (1- Cyanocyclopropane -1-carbonyl) -2,5- Dehydro -1H-pyrrole-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (1-cyanocyclopropane-1-carbonyl) -2,5-dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 362 (M + H) ⁺

Example  431: N- (4- (4- (3- Ethyl ureido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (3- ethylureido ) phenyl ) -1H- pyrrolo [2,3- b] pyridin-6-yl) cyclopropanecarboxamide)

N- (4- (4-aminophenyl) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (100 mg) was stirred with pyridine. 4 equivalents of ethyl isocyanate was added to the mixture, which was stirred for 12 hours at room temperature. After the reaction was completed, the mixture was added with d-HCl, extracted with dichloromethane, and the organic layer was separated. The mixture was concentrated, then dissolved in a MeOH / THF (1: 1) solution, 2N aqueous sodium hydroxide solution was added and stirred at 30-40 ^° C. for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and saturated aqueous ammonium chloride solution was added with stirring. The resulting solid was filtered to give the product N- (4- (4- (3-ethylureido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide It was.

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 8.68 (s, 1H), 7.98 (s, 1H), 7.58 (q, J = 8.2, 8.7 Hz, 4H), 7.37 (s, 1H), 6.55 (s, 1H), 6.22 (s, 1H), 5.75 (s, 1H), 3.14 (d, J = 6.4 Hz, 2H), 2.04 (s, 1H ), 1.07 (t, J = 6.7 Hz, 3H), 0.88-0.75 (m, 4H).

MS (ESI +) m / z 364 (M + H) ⁺

432 to 453 in the implementation

Hereinafter, in Examples 432 to 453, the synthesis was carried out in the same manner as in Example 431, or by using a suitable reactant in consideration of Scheme 1 and the structure of the compound to be prepared.

Example  432: N- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) morpholine-4-carboxamide (N- (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl) morpholine-4-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (s, 1H), 10.57 (s, 1H), 8.73 (s, 1H), 8.00 (s, 1H), 7.73-7.56 (m, 4H), 7.37 (d, J = 3.5 Hz, 1H), 6.56 (d, J = 3.2 Hz, 1H), 3.63 (s, 4H), 3.46 (s, 4H), 2.04 (s, 1H), 0.87-0.78 (m , 4H).

MS (ESI +) m / z 406 (M + H) ⁺

Example  433: N- (4- (4- (3- Butyl ureido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (3- butylureido ) phenyl ) -1H- pyrrolo [2,3- b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.56 (s, 1H), 8.63 (s, 1H), 7.98 (s, 1H), 7.70-7.51 (m, 5H), 7.46-7.36 (m, 1H), 6.55 (s, 1H), 6.21 (d, J = 5.7 Hz, 1H), 3.19-3.07 (m, 2H), 2.05 (s, 1H), 1.37 (ddd, J = 7.0, 14.2, 40.2 Hz, 5H), 0.90 (t, J = 7.2 Hz, 4H), 0.88-0.73 (m, 4H).

MS (ESI +) m / z 392 (M + H) ⁺

Example  434: N- (4- (4- (3- (4- Fluorophenyl ) Ureido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (3- (4-fluorophenyl) ureido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.58 (s, 1H), 9.07-8.95 (m, 1H), 8.87 (s, 1H), 8.01 (s, 1H), 7.65 (q, J = 8.6 Hz, 4H), 7.49 (dd, J = 5.3, 8.8 Hz, 2H), 7.39 (s, 1H), 7.13 (t, J = 8.6 Hz, 2H), 6.61-6.53 (m , 1H), 3.60 (s, 1H), 2.05 (s, 1H), 1.76 (s, 1H), 1.24 (s, 2H), 0.81 (d, J = 16.8 Hz, 4H).

MS (ESI +) m / z 380 (M + H) ⁺

Example  435: N- (4- (4- (3- (2,2,2- Trifluoroethyl ) Ureido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (3- (2,2,2-trifluoroethyl) ureido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6- yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 10.59 (s, 1H), 9.07 (s, 1H), 7.99 (s, 1H), 7.61 (q, J = 8.5 Hz, 4H), 7.38 (d, J = 3.1 Hz, 1H), 6.92 (s, 1H), 6.59-6.47 (m, 1H), 3.95 (dd, J = 6.5, 14.9 Hz, 2H), 2.03 (s, 1H ), 0.81 (s, 4H).

MS (ESI +) m / z 418 (M + H) ⁺

Example  436: N- (4- (2- methyl -4- (3- (2,2,2- Trifluoroethyl ) Ureido ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (2-methyl-4- (3- (2,2,2-trifluoroethyl) ) ureido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.61 (s, 1H), 8.92 (s, 1H), 7.76 (s, 1H), 7.41 (s, 1H), 7.33 ( dd, J = 5.7, 8.6 Hz, 2H), 7.17 (d, J = 8.3 Hz, 1H), 6.89 (s, 1H), 6.12-5.99 (m, 1H), 3.97-3.89 (m, 2H), 2.13 (s, 4H), 2.03 (s, 1H), 0.79 (s, 4H).

MS (ESI +) m / z 432 (M + H) ⁺

Example  437: N- (4- (4- (3- Cyclopropylureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (3- cyclopropylureido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 377 (M + H) ⁺

Example  438: N- (4- (4- (3- Ethyl ureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (3- ethylureido ) phenyl ) -7H- pyrrolo [2,3- d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 365 (M + H) ⁺

Example  439: N- (4- (4- (3- Butyl ureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (3- butylureido ) phenyl ) -7H- pyrrolo [2,3- d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 393 (M + H) ⁺

Example  440: N- (4- (4- (3- (3,4- Difluorophenyl ) Ureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (3- (3,4-difluorophenyl) ureido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) Synthesis of cyclopropanecarboxamide)

MS (ESI +) m / z 449 (M + H) ⁺

Example  441: N- (4- (4- (3- (4- Fluorophenyl ) Ureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (3- (4-fluorophenyl) ureido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide) Synthesis of

MS (ESI +) m / z 431 (M + H) ⁺

Example  442: N- (4- (4- (3- (2,2,2- Trifluoroethyl ) Ureido ) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (3- (2,2,2 -trifluoroethyl) ureido) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.50 (s, 1H), 7.86 (d, J = 3.9 Hz, 1H), 7.37-7.27 (m, 1H), 6.51 ( dd, J = 1.9, 3.6 Hz, 1H), 6.44 (t, J = 6.5 Hz, 1H), 6.33-6.19 (m, 2H), 3.83 (dq, J = 6.7, 9.8, 16.0 Hz, 3H), 2.15 1.88 (m, 3H), 1.68 (d, J = 9.0 Hz, 1H), 0.86-0.75 (m, 4H).

MS (ESI +) m / z 422 (M + H) ⁺

Example 443: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -N- (2,2,2-trifluoroethyl) -3,6-dihydropyridine-1 (2H) -carboxamide (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo Synthesis of [2,3-b] pyridin-4-yl) -N- (2,2,2-trifluoroethyl) -3,6-dihydropyridine-1 (2H) -carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.55 (s, 1H), 7.86 (s, 1H), 7.42-7.32 (m, 1H), 7.22 (t, J = 5.8 Hz, 1H), 6.54 (dd, J = 1.9, 3.7 Hz, 1H), 6.33 (s, 1H), 4.10 (s, 2H), 3.93-3.81 (m, 3H), 3.61 (t, J = 5.3 Hz , 2H), 2.02 (s, 1H), 0.82-0.75 (m, 4H).

MS (ESI +) m / z 408 (M + H) ⁺

Example  444: N-butyl-4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -3,6-dihydropyridine-1 (2H) -carboxamide (N-butyl-4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4- yl) -3,6-dihydropyridine-1 (2H) -carboxamide)

MS (ESI +) m / z 382 (M + H) ⁺

Example  445: N- (4- (1- (1,1- Deoxythiomorpholine -4-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1,1-dioxidothiomorpholine-4-carbonyl) -1 , 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (s, 1H), 7.87 (s, 1H), 7.34 (s, 1H), 6.56 (s, 1H), 6.34 ( s, 1H), 4.03 (d, J = 8.9 Hz, 2H), 3.63 (d, J = 18.8 Hz, 6H), 3.45 (s, 3H), 3.22-3.14 (m, 4H), 2.00 (s, 1H ), 1.20 (d, J = 25.7 Hz, 2H), 1.04 (d, J = 6.1 Hz, 2H), 0.80 (s, 4H).

MS (ESI +) m / z 444 (M + H) ⁺

Example  446: N- (4- (1- (morpholine-4-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (morpholine-4-carbonyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.53 (s, 1H), 7.86 (s, 1H), 7.34 (s, 1H), 6.56 (s, 1H), 6.34 ( s, 1H), 3.96 (s, 2H), 3.60 (s, 6H), 3.17 (d, J = 5.2 Hz, 4H), 2.02 (s, 1H), 1.04 (d, J = 5.6 Hz, 2H), 0.80 (s, 4 H).

MS (ESI +) m / z 396 (M + H) ⁺

Example  447: N- ( Cyanomethyl ) -4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -3,6-dihydropyridine-1 (2H) -carboxamide (N- (cyanomethyl) -4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin- Synthesis of 4-yl) -3,6-dihydropyridine-1 (2H) -carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (s, 1H), 7.85 (s, 1H), 7.34 (s, 1H), 6.54 (s, 1H), 6.31 ( s, 1H), 4.12 (s, 2H), 4.03 (d, J = 6.8 Hz, 1H), 3.65 (s, 3H), 3.63 (s, 2H), 2.00 (d, J = 12.2 Hz, 2H), 0.78 (d, J = 13.1 Hz, 4H).

MS (ESI +) m / z 365 (M + H) ⁺

Example  448: 3- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -N- (2,2,2-trifluoroethyl) -8- Azabicyclo [3.2.1] oct-2-ene-8-carboxamide (3- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3-b] pyridin -4- yl Synthesis of) -N- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] oct-2-ene-8-carboxamide)

MS (ESI +) m / z 434 (M + H) ⁺

Example  449 N-butyl-3- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -8-azabicyclo [3.2.1] oct-2-ene-8-carboxamide (N-butyl-3- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] Synthesis of pyridin-4-yl) -8-azabicyclo [3.2.1] oct-2-ene-8-carboxamide)

MS (ESI +) m / z 408 (M + H) ⁺

Example  450: 4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -N- (1-cyclopropyl-2,2,2-trifluoro Ethyl) -3,6-dihydropyridine-1 (2H) -carboxamide (4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3-b] pyridin -4- yl Synthesis of) -N- (1-cyclopropyl-2,2,2-trifluoroethyl) -3,6-dihydropyridine-1 (2H) -carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.81 (s, 1H), 10.05 (dd, J = 3.0, 8.9 Hz, 1H), 7.84 (d, J = 4.0 Hz, 1H), 7.81 (d, J = 4.8 Hz, 1H), 6.89 (d, J = 4.1 Hz, 1H), 6.36 (d, J = 4.6 Hz, 1H), 4.43 (d, J = 3.2 Hz, 1H), 4.32 (s, 1H) , 4.08 (p, J = 8.7 Hz, 1H), 3.93 (t, J = 5.5 Hz, 1H), 3.80 (t, J = 5.7 Hz, 1H), 2.68 (s, 2H), 1.94 (q, J = 6.2 Hz, 1H), 1.55 (dd, J = 6.6, 12.0 Hz, 1H), 1.16-1.10 (m, 1H), 0.92-0.86 (m, 4H), 0.72 (dd, J = 5.6, 22.3 Hz, 2H ), 0.64 (d, J = 25.9 Hz, 1H), 0.46-0.35 (m, 1H).

MS (ESI +) m / z 448 (M + H) ⁺

Example  451: N- (4- (1- (1H-imidazole-1-carbonyl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1H-imidazole-1-carbonyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.46 (s, 1H), 10.57 (s, 1H), 8.13 (s, 1H), 7.90 (s, 1H), 7.58 (d, J = 1.4 Hz, 1H), 7.36 (t, J = 3.0 Hz, 1H), 7.06 (s, 1H), 6.60 (d, J = 2.8 Hz, 1H), 6.34 (s, 1H), 4.29 (d, J = 3.6 Hz, 2H), 3.71 (d, J = 6.3 Hz, 2H), 2.72 (s, 2H), 1.99 (s, 1H), 0.85-0.69 (m, 4H).

MS (ESI +) m / z 377 (M + H) ⁺

Example  452: N- (4- (1- (1H-imidazole-1-carbonyl) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1H-imidazole-1-carbonyl) -3-methyl -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.57 (s, 1H), 8.13 (s, 1H), 7.85 (s, 1H), 7.58 (d, J = 1.8 Hz, 1H), 7.38-7.30 (m, 1H), 7.07 (s, 1H), 6.59-6.50 (m, 1H), 6.10 (s, 1H), 4.37-4.22 (m, 2H), 3.70 (s, 2H) , 3.14 (s, 1H), 2.00 (d, J = 15.8 Hz, 1H), 0.90 (d, J = 7.0 Hz, 3H), 0.85-0.72 (m, 4H).

MS (ESI +) m / z 391 (M + H) ⁺

Example 453: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3-methyl-N- (2,2,2-trifluoroethyl) -3,6-dihydropyridine-1 (2H) -carboxamide (4- (6- (cyclopropanecarboxamido) Synthesis of -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-methyl-N- (2,2,2-trifluoroethyl) -3,6-dihydropyridine-1 (2H) -carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.56 (s, 1H), 7.83 (s, 1H), 7.39-7.30 (m, 1H), 7.25-7.16 (m, 1H ), 6.46 (dd, J = 2.0, 3.6 Hz, 1H), 6.10 (d, J = 3.5 Hz, 1H), 4.23 (d, J = 18.2 Hz, 1H), 3.99-3.84 (m, 3H), 3.62 -3.49 (m, 2H), 2.94 (s, 1H), 2.03 (d, J = 8.3 Hz, 1H), 0.86 (d, J = 6.9 Hz, 3H), 0.82-0.73 (m, 4H).

MS (ESI +) m / z 422 (M + H) ⁺

Example  454: tert - Butyl 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3,6-dihydropyridine-1 (2H) -carboxylate ( tert - butyl  Synthesis of 4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6-dihydropyridine-1 (2H) -carboxylate)

[Step 1]

N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1-tosyl-1H-pyrrolo [2, 3-b] pyridin-6-yl) cyclopropanecarboxamide 4.0 g (8.3 mmol) is dissolved in DMF / H ₂ O = 2: 1 solution and tert-butyl-4-(((trifluoromethyl) Sulfonyl) oxy) -3,6-dihydropyridine-1 (2H) -carboxylate 3.3 g (10.0 mmol), Pd (PPh ₃ ) ₄ 0.9 g (0.8 mmol), 2M K ₂ CO ₃ aqueous solution 0.57 mL Was added and stirred for 2 hours at 100 ~ 110 ^o C. When the reaction was completed, the mixture was cooled to room temperature, water was added, and extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was separated by NH-silica gel column chromatography (n-hexane / ethylacetate = 5: 1), tert-butyl4- (6- (cyclopropanecarboxamido) -1-tosyl-1H-pyrrolo [ 2,3-b] pyridin-4-yl) -3,6-dihydropyridine-1- (2H) -carboxylate was obtained.

MS (ESI +) m / z 537 (M + H) ⁺

[Step 2]

The synthesized material was dissolved in MeOH / THF (1: 1) solution and 2N aqueous sodium hydroxide solution was added and stirred at 30-40 ^° C. for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and saturated aqueous ammonium chloride solution was added with stirring. The resulting solid was filtered to give the product tert-butyl4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6-dihydropyridine- 1 (2H) -carboxylate was obtained.

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.53 (s, 1H), 7.86 (s, 1H), 7.43-7.26 (m, 1H), 6.61-6.45 (m, 1H ), 6.31 (s, 1H), 4.07 (s, 2H), 3.67-3.46 (m, 2H), 2.59-2.52 (m, 2H), 2.02 (td, J = 3.7, 7.8 Hz, 1H), 1.44 ( s, 9H), 0.80 (dt, J = 5.9, 12.2 Hz, 4H).

MS (ESI +) m / z 383 (M + H) ⁺

Example  455 to 461

Hereinafter, in Examples 455 to 461, the synthesis was carried out in the same manner as in Example 454, or synthesized using an appropriate reactant in consideration of Scheme 1 and the structure of the compound to be prepared.

Example  455: Cyanomethyl4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3,6-dihydropyridine-1 (2H) -carboxylate ( cyanomethyl  Synthesis of 4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6-dihydropyridine-1 (2H) -carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.56 (s, 1H), 7.87 (s, 1H), 7.41-7.30 (m, 1H), 6.56 (dd, J = 1.9 , 3.6 Hz, 1H), 6.32 (d, J = 14.8 Hz, 1H), 4.98 (s, 2H), 4.16 (s, 2H), 3.67 (q, J = 5.6, 7.9 Hz, 2H), 2.58 (s , 3H), 2.02 (s, 1H), 0.85-0.73 (m, 4H).

MS (ESI +) m / z 366 (M + H) ⁺

Example  456: tert -Butyl 4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3-methyl-3,6-dihydropyridine-1 (2H) -carboxylate ( tert - butyl  Synthesis of 4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-methyl-3,6-dihydropyridine-1 (2H) -carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.56 (s, 1H), 7.83 (s, 1H), 7.32 (t, J = 3.1 Hz, 1H), 6.48 (d, J = 3.0 Hz, 1H), 6.08 (s, 1H), 4.25 (s, 1H), 3.88 (s, 1H), 3.68-3.37 (m, 2H), 2.92 (s, 1H), 2.01 (s, 1H ), 0.86 (d, J = 6.7 Hz, 3H), 0.81-0.71 (m, 4H).

MS (ESI +) m / z 397 (M + H) ⁺

Example  457: tert - Butyl 4 -(6- ( Cyclopropanecarboxamido ) -5- methyl -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3,6-dihydropyridine-1 (2H) -carboxylate ( tert - butyl  Synthesis of 4- (6- (cyclopropanecarboxamido) -5-methyl-1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6-dihydropyridine-1 (2H) -carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.03 (s, 1H), 7.34 (t, J = 2.9 Hz, 1H), 6.23 (dd, J = 3.5, 1.9 Hz, 1H), 5.66 (s, 1H), 4.03 (s, 2H), 3.61 (d, J = 5.7 Hz, 2H), 2.30 (s, 2H), 2.08 (s, 3H), 1.45 (s, 9H), 0.76 (d, J = 6.2 Hz, 4H).

MS (ESI +) m / z 397 (M + H) ⁺

Example  458: tert -Butyl 4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3-ethyl-3,6-dihydropyridine-1 (2H) -carboxylate ( tert - butyl  Synthesis of 4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-ethyl-3,6-dihydropyridine-1 (2H) -carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.55 (s, 1H), 7.83 (s, 1H), 7.42-7.25 (m, 1H), 6.58-6.48 (m, 1H ), 6.11 (s, 1H), 4.33 (dd, J = 19.3, 44.4 Hz, 1H), 4.10-3.67 (m, 2H), 3.21 (dd, J = 3.7, 13.1 Hz, 1H), 2.67 (d, J = 1.7 Hz, 1H), 2.02 (s, 1H), 1.44 (s, 9H), 1.22 (d, J = 15.5 Hz, 3H), 0.87-0.73 (m, 7H).

MS (ESI +) m / z 411 (M + H) ⁺

Example  459: tert - Butyl 5 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3,4-dihydropyridine-1 (2H) -carboxylate ( tert - butyl  Synthesis of 5- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,4-dihydropyridine-1 (2H) -carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.46 (s, 1H), 7.85 (s, 1H), 7.68 (s, 1H), 7.33 (s, 1H), 6.48 ( dd, J = 3.5, 1.9 Hz, 1H), 3.59 (s, 2H), 2.46 (s, 2H), 2.01 (q, J = 6.3 Hz, 1H), 1.93 (t, J = 6.0 Hz, 2H), 0.85-0.71 (m, 4H).

MS (ESI +) m / z 383 (M + H) ⁺

Example  460: tert - Butyl 5 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3,6-dihydropyridine-1 (2H) -carboxylate ( tert - butyl  Synthesis of 5- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6-dihydropyridine-1 (2H) -carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.46 (s, 1H), 10.55 (s, 1H), 7.84 (s, 1H), 7.35 (t, J = 3.0 Hz, 1H), 6.52 (s, 1H), 6.39 (s, 1H), 4.26 (s, 2H), 3.53 (t, J = 5.8 Hz, 2H), 2.34 (td, J = 6.9, 6.3, 2.8 Hz, 2H), 2.02 (tt, J = 7.5, 4.5 Hz, 1H), 1.43 (s, 9H), 0.80 (ddt, J = 10.9, 5.4, 3.0 Hz, 4H).

MS (ESI +) m / z 383 (M + H) ⁺

Example  461: tert - Butyl 3 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -2,5-dihydro-1H-pyrrole-1-carboxylate ( tert - butyl  Synthesis of 3- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -2,5-dihydro-1H-pyrrole-1-carboxylate)

MS (ESI +) m / z 369 (M + H) ⁺

Example  462: N- (4- (4- (3- Ethylthioureido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (3- ethylthioureido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

N- (4- (4-aminophenyl) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (100 mg) was stirred with pyridine. 4 equivalents of ethyl isothiocyanate was added to the mixture, which was stirred for 16 hours at 50-60 ^° C. After the reaction was completed, the mixture was concentrated, dissolved in a MeOH / THF (1: 1) solution, 2N aqueous sodium hydroxide solution was added, and stirred at 30-40 ^° C. for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and saturated aqueous ammonium chloride solution was added with stirring. The resulting solid was filtered to give the product N- (4- (4- (3-ethylthioureido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide Obtained.

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.60 (s, 1H), 9.71 (s, 1H), 7.99 (d, J = 23.1 Hz, 2H), 7.63 (dd, J = 8.6, 31.6 Hz, 4H), 7.40 (s, 1H), 6.55 (d, J = 3.5 Hz, 1H), 2.05 (s, 1H), 1.25-1.13 (m, 3H), 0.82 (d, J = 7.6 Hz, 4H).

MS (ESI +) m / z 380 (M + H) ⁺

Example  463 to 469

Hereinafter, in Examples 463 to 469, the synthesis was carried out in the same manner as in Example 462, or synthesized using an appropriate reactant in consideration of Scheme 1 and the structure of the compound to be prepared.

Example  463: N- (4- (4- (3- Butylthioureido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (3- butylthioureido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.69 (s, 1H), 9.78 (s, 1H), 7.99 (s, 2H), 7.65 (q, J = 8.5 Hz, 3H), 7.41 (d, J = 3.1 Hz, 1H), 6.57 (d, J = 3.3 Hz, 1H), 3.49 (s, 2H), 2.06 (d, J = 13.5 Hz, 1H), 1.60-1.49 ( m, 2H), 1.34 (q, J = 7.4 Hz, 2H), 1.24 (s, 1H), 0.92 (t, J = 7.2 Hz, 3H), 0.83 (d, J = 6.8 Hz, 4H).

MS (ESI +) m / z 408 (M + H) ⁺

Example  464: N- (4- (4- (3- Cyclohexylthioureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine Synthesis of 2-yl) cyclopropanecarboxamide (N- (4- (4- (3-cyclohexylthioureido) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 435 (M + H) ⁺

Example  465: N- (4- (4- (3- Butylthioureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (3- butylthioureido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 409 (M + H) ⁺

Example  466: N- (4- (4- (3- Ethylthioureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (3- ethylthioureido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 381 (M + H) ⁺

Example  467: N- (4- (4- (3- Profile Thioureido ) Phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (3- propylthioureido ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 395 (M + H) ⁺

Example  468: N- (4- (1- ( Ethylcarbamothioyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (ethylcarbamothioyl) -1,2,3,6-tetrahydropyridin Synthesis of -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 370 (M + H) ⁺

Example  469: N- (4- (8- ( Ethylcarbamothioyl )-8- Azabicyclo [3.2.1] oct -2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (ethylcarbamothioyl) -8-azabicyclo [3.2 .1] oct-2-en-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 396 (M + H) ⁺

Example  470: N- (4- (4-(( Cyclopropylmethyl ) Amino) phenyl) -1H- Pyrrolo [2,3-b] pyridine Preparation of -6-yl) cyclopropanecarboxamide (N- (4- (4-((cyclopropylmethyl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

N- (4- (4-aminophenyl) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (100 mg) is dissolved in dichloroethane and cyclo 3 equivalents of propanecarbaldehyde and 3 equivalents of acetic acid were added and stirred at room temperature for 30 minutes. 3 equivalents of sodium triacetoxyborohydride was added to the reaction mixture, and the mixture was stirred at 40 ^° C. for 16 hours. When the reaction was completed, the mixture was concentrated, dissolved in MeOH / THF (1: 1) solution, 2N aqueous sodium hydroxide solution was added, and stirred for 4 hours at 30 ~ 40 ^° C. Upon completion of the reaction, the mixture was cooled at room temperature and extracted with dichloromethane. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue is prep. Target compound N- (4- (4-((cyclopropylmethyl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl via TLC (DCM: MeOH = 30: 1) method ) Cyclopropanecarboxamide was obtained.

MS (ESI +) m / z 347 (M + H) ⁺

Example  471 to 489

Hereinafter, in Examples 471 to 489, the synthesis was carried out in the same manner as in Example 470, or synthesized using an appropriate reactant in consideration of Scheme 1 and the structure of the compound to be prepared.

Example  471: N- (4- (4-(( Cyclohexylmethyl ) Amino) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-(( cyclohexylmethyl ) amino ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.50 (s, 1H), 7.92 (s, 1H), 7.48 (d, J = 8.6 Hz, 2H), 7.32 (dd, J = 2.4, 3.5 Hz, 1H), 6.69 (d, J = 8.5 Hz, 2H), 6.54 (dd, J = 1.9, 3.5 Hz, 1H), 6.02 (t, J = 5.7 Hz, 1H), 3.64- 3.55 (m, 2H), 2.91 (t, J = 6.2 Hz, 2H), 2.03 (s, 1H), 1.82-1.52 (m, 7H), 1.25-1.12 (m, 3H), 0.95 (q, J = 12.0, 12.5 Hz, 2H), 0.86-0.72 (m, 4H).

MS (ESI +) m / z 389 (M + H) ⁺

Example  472: N- (4- (4- ( Benzylamino ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  (N- (4- (4- ( benzylamino ) phenyl ) -1H- pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.50 (s, 1H), 7.91 (s, 1H), 7.46 (d, J = 8.6 Hz, 2H), 7.42-7.28 ( m, 5H), 7.24 (t, J = 7.3 Hz, 1H), 6.73 (d, J = 8.6 Hz, 2H), 6.63 (t, J = 6.0 Hz, 1H), 6.52 (dd, J = 1.8, 3.5 Hz, 1H), 4.34 (d, J = 6.0 Hz, 2H), 2.02 (s, 1H), 0.83-0.72 (m, 4H).

MS (ESI +) m / z 383 (M + H) ⁺

Example  473: N- (4- (4-((4- Fluorobenzyl ) Amino) phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((4- fluorobenzyl ) amino ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 402 (M + H) ⁺

Example  474: N- (4- (4-((3- Fluorobenzyl ) Amino) phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((3- fluorobenzyl ) amino ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 402 (M + H) ⁺

Example  475: N- (4- (4-((4- Chlorobenzyl ) Amino) phenyl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4-((4- chlorobenzyl ) amino ) phenyl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 418, 420 (M + H) ⁺

Example  476: N- (4- (4-((3-hydroxypropyl) amino) phenyl) -7H- Pyrrolo [2,3-d] pyrimidine Synthesis of-2-yl) cyclopropanecarboxamide (N- (4- (4-((3-hydroxypropyl) amino) phenyl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 352 (M + H) ⁺

Example  477: N- (4- (1- (2- Cyanoethyl ) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (2- cyanoethyl ) -1H- pyrazol -4- yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.53 (s, 1H), 8.50 (s, 1H), 8.06 (d, J = 9.1 Hz, 2H), 7.48-7.35 ( m, 1H), 7.00 (s, 1H), 6.72 (d, J = 4.1 Hz, 1H), 4.57-4.45 (m, 2H), 3.22-3.11 (m, 2H), 2.05 (s, 1H), 0.82 (d, J = 12.2 Hz, 4H).

MS (ESI +) m / z 321 (M + H) ⁺

Example  478: N- (4- (1- ( Cyclopropylmethyl ) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- ( cyclopropylmethyl ) -1H- pyrazol Synthesis of -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (d, J = 12.3 Hz, 1H), 10.51 (s, 1H), 8.39 (s, 1H), 8.01 (d, J = 32.6 Hz, 2H) , 7.48-7.31 (m, 1H), 6.72 (s, 1H), 4.06 (d, J = 7.7 Hz, 2H), 2.04 (s, 1H), 1.33 (s, 1H), 0.89-0.74 (m, 4H ), 0.62-0.38 (m, 4H).

MS (ESI < + >) m / z 322 (M + H) ⁺

Example  479: N- (4- (1- benzyl -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  (N- (4- (1- benzyl -1H- pyrazol -4- yl ) -1H- pyrrolo [2,3- b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.50 (s, 1H), 8.54 (s, 1H), 8.09-7.91 (m, 3H), 7.35 (d, J = 13.5 Hz, 8H), 7.23 (s, 1H), 6.71 (s, 1H), 5.42 (d, J = 4.1 Hz, 2H), 2.03 (s, 1H), 0.82 (s, 4H).

MS (ESI +) m / z 358 (M + H) ⁺

Example  480: N- (4- (1- (2- Cyanoethyl ) -3,5-dimethyl-1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoethyl) -3,5-dimethyl-1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b] Synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.55 (s, 1H), 7.72 (s, 1H), 7.32 (s, 1H), 6.14 (s, 1H), 4.33 ( d, J = 5.9 Hz, 2H), 3.06 (d, J = 5.9 Hz, 2H), 2.27-2.17 (m, 3H), 2.10 (s, 3H), 2.02 (s, 1H), 0.78 (d, J = 12.9 Hz, 4H).

MS (ESI +) m / z 349 (M + H) ⁺

Example  481: N- (4- (1- benzyl -1H-1,2,3- Triazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- benzyl -1H-1,2,3- triazol -4- yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.58 (s, 1H), 8.93 (s, 1H), 8.40 (s, 1H), 7.51-7.30 (m, 6H), 6.88 (dd, J = 3.5, 1.9 Hz, 1H), 5.69 (s, 2H) 2.10-1.95 (m, 1H), 0.96-0.72 (m, 4H).

MS (ESI +) m / z 421 (M + H) ⁺

Example  482: N- (4- (1-((6- Cyanopyridine -3 days) methyl ) -1H- Pyrazole -4-yl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (1-((6-cyanopyridin-3-yl) methyl) -1H-pyrazol-4-yl) -7H-pyrrolo [2,3-d ] Synthesis of pyrimidin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.92 (s, 1H), 10.42 (s, 1H), 9.16 (s, 1H), 8.78 (s, 1H), 8.71 (d, J = 2.1 Hz, 1H), 8.29 (d, J = 3.3 Hz, 1H), 7.88-7.76 (m, 2H), 7.43 (d, J = 3.8 Hz, 1H), 6.87 (d, J = 3.8 Hz, 1H), 5.60 ( d, J = 6.2 Hz, 2H), 2.20 (s, 1H), 0.80 (ddt, J = 3.0, 4.9, 10.7 Hz, 4H).

MS (ESI +) m / z 385 (M + H) ⁺

Example  483: N- (4- (1- (2- Cyanoethyl ) -1H-pyrrole-3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (2- cyanoethyl ) -1H- pyrrol -3- yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.30 (s, 1H), 10.44 (s, 1H), 8.01 (s, 1H), 7.56 (d, J = 2.1 Hz, 1H), 7.31 (d, J = 2.5 Hz, 1H), 6.98 (t, J = 2.5 Hz, 1H), 6.71 (d, J = 3.2 Hz, 1H), 6.54 (d, J = 2.5 Hz, 1H), 4.27 (t, J = 6.5 Hz, 2H), 3.09 (t, J = 6.4 Hz, 2H), 2.03 (s, 1H), 0.83-0.76 (m, 4H).

MS (ESI +) m / z 320 (M + H) ⁺

Example  484: N- (4- (1- (2- Morpholinoethyl ) -2,5- Dehydro -1H-pyrrole-3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (2-morpholinoethyl) -2,5-dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] Synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.56 (s, 1H), 10.61 (s, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.42 (d, J = 3.1 Hz, 1H) , 6.81-6.64 (m, 2H), 4.55 (d, J = 10.5 Hz, 2H), 4.37 (s, 2H), 4.19 (t, J = 6.7 Hz, 2H), 3.57 (d, J = 4.7 Hz, 4H), 2.59 (d, J = 6.2 Hz, 2H), 2.45 (d, J = 4.6 Hz, 2H), 2.03 (s, 1H), 0.84-0.74 (m, 4H).

MS (ESI +) m / z 382 (M + H) ⁺

Example  485: N- (4- (1- (2- Cyanoethyl ) -2,5- Dehydro -1H-pyrrole-3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoethyl) -2,5-dihydro-1H-pyrrol-3-yl) -1H-pyrrolo [2,3-b] Synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.55 (s, 1H), 7.80 (s, 1H), 7.38 (t, J = 3.0 Hz, 1H), 6.67-6.57 ( m, 2H), 3.93 (q, J = 3.7 Hz, 2H), 3.73 (td, J = 2.1, 4.5 Hz, 2H), 2.94 (t, J = 6.7 Hz, 2H), 2.73 (t, J = 6.7 Hz, 2H), 2.02 (tt, J = 4.5, 7.7 Hz, 1H), 0.80 (ddd, J = 2.8, 5.3, 11.3 Hz, 4H).

MS (ESI < + >) m / z 322 (M + H) ⁺

Example  486: N- (4- (1- (2- Cyanoethyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2-cyanoethyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (s, 1H), 10.50 (s, 1H), 7.86 (s, 1H), 7.33 (d, J = 2.7 Hz, 1H), 6.54 (d, J = 3.5 Hz, 1H), 6.32 (s, 1H), 3.23 (t, J = 3.1 Hz, 2H), 2.73 (dd, J = 4.5, 7.5 Hz, 5H), 2.02 (s, 1H), 0.82- 0.75 (m, 4 H).

MS (ESI +) m / z 336 (M + H) ⁺

Example  487: N- (4- (1-((3- Methyloxetane -3 days) methyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] cyclopropanecarboxamide (N- (4- (1-((3-methyloxetan-3-yl) methyl) -1,2,3, Synthesis of 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 367 (M + H) ⁺

Example  488: N- (4- (1- ( Isothiazole -5- Methyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (isothiazol-5-ylmethyl) -1,2,3 , 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.53 (s, 1H), 8.50 (d, J = 1.6 Hz, 1H), 7.86 (s, 1H), 7.33 (d, J = 2.1 Hz, 2H), 6.55 (d, J = 2.7 Hz, 1H), 6.33 (s, 1H), 3.29 (d, J = 3.4 Hz, 2H), 2.77 (t, J = 5.6 Hz, 2H) , 2.56 (s, 2H), 2.01 (d, J = 4.1 Hz, 1H), 0.88-0.72 (m, 4H).

MS (ESI +) m / z 380 (M + H) ⁺

Example  489: N- (4- (1-((2,2- Difluorocyclopropyl ) methyl ) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1-((2,2-difluorocyclopropyl) methyl) -1, 2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.52 (s, 1H), 7.85 (s, 1H), 7.35-7.29 (m, 1H), 6.54 (dd, J = 3.5 , 1.8 Hz, 1H), 6.33 (d, J = 3.4 Hz, 1H), 3.25-3.19 (m, 2H), 2.72 (dp, J = 16.1, 5.4 Hz, 3H), 2.50 (m, 3H), 2.01 (s, 1H), 1.90 (tt, J = 13.8, 6.9 Hz, 1H), 1.62 (qt, J = 12.1, 5.9 Hz, 1H), 1.19 (dd, J = 7.9, 3.8 Hz, 1H), 0.87- 0.72 (m, 4H)

MS (ESI +) m / z 373 (M + H) ⁺

Example  490: N- (4- (1-(-3- Cyanocyclobutyl ) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3-cyanocyclobutyl) -1,2,3,6 -tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

1.0 g (3.37 mmol) of synthesized N- (4- (4-aminocyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ), 3-oxocyclobutane-1-carbonitrile was dissolved in THF solution, NaBH (OAc) ₃ and DIPEA were added and stirred for 1 day at room temperature. When the reaction was completed, water was added and extracted with dichloromethane. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was separated by silica gel column chromatography to obtain N- (4- (4-((1- (3,5-difluorobenzoyl) piperidin-4-yl) amino) cyclohex-1-ene-1 -Yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide was obtained.

MS (ESI +) m / z 362 (M + H) ⁺

Example  491 to 518

Hereinafter, in Examples 491 to 518, the synthesis was carried out in the same manner as in Example 490, or synthesized using an appropriate reactant in consideration of Scheme 1 and the structure of the compound to be prepared.

Example  491: N- (4- (4-((1- (3,5- Difluorobenzoyl ) Piperidin-4-yl) amino) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- (3,5- Synthesis of difluorobenzoyl) piperidin-4-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.35 (s, 1H), 10.48 (s, 1H), 7.82 (s, 1H), 7.38-7.20 (m, 2H), 7.17-7.10 (m, 2H) , 6.48 (dd, J = 3.5, 1.8 Hz, 1H), 6.23 (s, 1H), 4.28 (s, 1H), 3.47 (s, 1H), 2.98 (s, 3H), 2.00 (s, 3H), 1.81 (s, 1 H), 1.48 (s, 2 H), 1.25 (d, J = 9.2 Hz, 5H), 0.82-0.74 (m, 4H).

MS (ESI +) m / z 520 (M + H) ⁺

Example  492: N- (4- (4-((1- ( Cyclohexanecarbonyl ) Piperidin-4-yl) amino) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- (cyclohexanecarbonyl) piperidin- Synthesis of 4-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.35 (s, 1H), 10.48 (s, 1H), 7.82 (s, 1H), 7.30 (t, J = 3.0 Hz, 1H), 6.49 (dd, J = 3.6, 1.9 Hz, 1H), 6.22 (s, 1H), 4.26 (d, J = 13.7 Hz, 1H), 3.88 (d, J = 13.5 Hz, 1H), 3.56 (t, J = 7.0 Hz, 1H ), 3.14 (dd, J = 7.5, 5.6 Hz, 1H), 2.19 (d, J = 6.7 Hz, 1H), 2.01 (s, 4H), 1.70 (d, J = 11.1 Hz, 4H), 1.61 (t , J = 6.9Hz, 6H), 1.30 (s, 6H), 1.18 (d, J = 9.8Hz, 2H), 1.07 (t, J = 7.2Hz, 2H), 0.82-0.77 (m, 4H)

MS (ESI +) m / z 490 (M + H) ⁺

Example  493: N- (4- (4-((1- (2- Fluoroisonicotinoyl ) Piperidin-4-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] cyclopropane Carboxamide  (N- (4- (4-((1- (2-fluoroisonicotinoyl) piperidin-4-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.36 (s, 1H), 10.48 (s, 1H), 8.33 (d, J = 5.0 Hz, 1H), 7.82 (s, 1H), 7.32 (dt, J = 18.3, 3.9Hz, 2H), 7.23 (s, 1H), 6.49 (dd, J = 3.6, 1.9Hz, 1H), 6.22 (s, 1H), 4.32 (d, J = 12.7Hz, 1H), 3.43 (d, J = 13.8 Hz, 1H), 3.04 (dt, J = 39.7, 12.3 Hz, 4H), 1.98 (d, J = 22.7 Hz, 4H), 0.84-0.75 (m, 4H)

MS (ESI +) m / z 503 (M + H) ⁺

Example  494: N- (4- (4-((1- (4- Nitrobenzoyl ) Piperidin-4-yl) amino) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane Carboxamide  (N- (4- (4-((1- (4-nitrobenzoyl) piperidin-4-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.35 (d, J = 3.2 Hz, 1H), 10.48 (s, 1H), 8.32-8.25 (m, 2H), 7.82 (s, 1H), 7.71-7.59 (m, 2H), 7.29 (t, J = 3.1 Hz, 1H), 6.48 (dd, J = 3.5, 1.9 Hz, 1H), 6.22 (s, 1H), 4.32 (d, J = 12.4 Hz, 1H) , 3.43 (d, J = 13.3Hz, 1H), 3.03 (d, J = 52.9Hz, 4H), 2.00 (d, J = 7.2Hz, 4H), 1.78 (s, 1H), 1.47 (s, 2H) , 1.25 (d, J = 17.8Hz, 4H), 0.85-0.73 (m, 4H)

MS (ESI +) m / z 529 (M + H) ⁺

Example  495: N- (4- (4-((1- (3,5- Difluorobenzoyl ) Azetidine -3-yl) amino) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- (3,5- Synthesis of difluorobenzoyl) azetidin-3-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.35 (s, 1H), 10.47 (s, 1H), 7.43 (tt, J = 9.5, 2.5 Hz, 1H), 7.30 (dq, J = 5.8, 2.1 Hz , 3H), 7.19 -7.12 (m, 1H), 6.48 (t, J = 2.7Hz, 1H), 6.21 (d, J = 4.1Hz, 1H), 4.47 (d, J = 8.4Hz, 1H), 4.22 (d, J = 10.5Hz, 1H), 4.03 (s, 1H), 3.78 (dd, J = 7.0, 3.8Hz, 2H), 3.63 (t, J = 7.0Hz, 1H), 3.01 (qd, J = 7.2, 5.3 Hz, 1H), 1.91 (d, J = 6.9 Hz, 1H), 0.83-0.72 (m, 4H)

MS (ESI +) m / z 492 (M + H) ⁺

Example  496: N- (4- (4-((1- (2- Fluoroisonicotinoyl ) Azetidine -3-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane Carboxamide  (N- (4- (4-((1- (2-fluoroisonicotinoyl) azetidin-3-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.35 (s, 1H), 10.48 (s, 1H), 8.34 (dd, J = 22.8, 5.1 Hz, 1H), 7.82 (s, 1H), 7.52 (dt , J = 5.1, 1.6Hz, 1H), 7.33 (t, J = 1.7Hz, 1H), 7.29 (t, J = 3.1Hz, 1H), 6.47 (dt, J = 3.7, 2.0Hz, 1H), 6.21 (s, 1H), 4.46 (td, J = 7.6, 6.5, 3.9 Hz, 1H), 4.24 (d, J = 10.7 Hz, 1H), 4.04-4.01 (m, 1H), 3.79 (dt, J = 7.7 , 4.2Hz, 2H), 3.00 (ddd, J = 8.6, 6.9, 5.3Hz, 1H), 2.80 (s, 1H), 2.18 (t, J = 3.4Hz, 1H), 2.03-1.99 (m, 2H) , 1.91 (d, J = 5.9 Hz, 1H), 0.82-0.74 (m, 4H)

MS (ESI < + >) m / z 475 (M + H) ⁺

Example  497: N- (4- (4-((1- (2- Methoxyisonicotinoyl ) Azetidine -3-yl) amino) Cyclohex -1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane Carboxamide  (N- (4- (4-((1- (2-methoxyisonicotinoyl) azetidin-3-yl) amino) cyclohex-1-en-1-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.35 (s, 1H), 10.48 (s, 1H), 8.27 (d, J = 5.3 Hz, 1H), 7.81 (s, 1H), 7.33-7.26 (m , 1H), 7.12 (dd, J = 5.2, 1.4 Hz, 1H), 6.92 (t, J = 1.0 Hz, 1H), 6.53-6.43 (m, 1H), 6.21 (s, 1H), 4.43 (s, 1H), 4.23 (s, 1H), 3.99 (s, 1H), 3.78 (s, 2H), 2.81 (s, 1H), 2.00 (d, J = 5.4 Hz, 2H), 1.91 (s, 1H), 1.48 (s, 2 H), 0.81-0.74 (m, 4 H)

MS (ESI +) m / z 487 (M + H) ⁺

Example 498: 4 -((4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -2-fluorophenyl) amino) -N-phenylpiperidine-1-carboxamide (4-((4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b ] Synthesis of pyridin-4-yl) -2-fluorophenyl) amino) -N-phenylpiperidine-1-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.54 (s, 1H), 8.52 (s, 1H), 7.95 (s, 1H), 7.51-7.45 (m, 2H), 7.42 -7.33 (m, 3H), 7.25-7.19 (m, 2H), 7.00 (t, J = 8.8 Hz, 1H), 6.94-6.87 (m, 1H), 6.56 (dd, J = 3.5, 1.9 Hz, 1H ), 5.61 (d, J = 7.9 Hz, 1H), 4.15 (d, J = 13.3 Hz, 2H), 3.61 (s, 1H), 2.96 (t, J = 12.5 Hz, 2H), 2.04 (s, 1H ), 1.94 (t, J = 14.5 Hz, 2H), 1.52-1.42 (m, 3H), 1.23 (s, 6H), 0.82 (dd, J = 8.8, 5.0 Hz, 4H).

MS (ESI +) m / z 513 (M + H) ⁺

Example  499: N- (4- (4-((1- (3,5- Difluorobenzoyl ) Piperidin-4-yl) amino) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- Synthesis of ((1- (3,5-difluorobenzoyl) piperidin-4-yl) amino) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 534 (M + H) ⁺

Example  500: N- (4- (3- Fluoro -4-((1- (2- Fluoroisonicotinoyl ) Piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (3-fluoro-4- ( Synthesis of (1- (2-fluoroisonicotinoyl) piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.55 (s, 1H), 8.35 (d, J = 5.0 Hz, 1H), 7.94 (s, 1H), 7.42-7.28 (m , 3H), 7.24 (s, 1H), 6.99 (s, 1H), 6.58-6.48 (m, 1H), 5.55 (d, J = 9.0 Hz, 1H), 5.32 (s, 1H), 2.01 (t, J = 7.5 Hz, 4H), 1.91 (s, 1H), 1.56-1.39 (m, 4H), 1.23 (s, 9H), 0.83 (d, J = 14.1 Hz, 4H).

MS (ESI +) m / z 517 (M + H) ⁺

Example 501: 4 -((4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -2-fluorophenyl) amino) -N- (2,4-difluorophenyl) piperidine-1-carboxamide (4-((4- (6- (cyclopropanecarboxamido)- Synthesis of 1H-pyrrolo [2,3-b] pyridin-4-yl) -2-fluorophenyl) amino) -N- (2,4-difluorophenyl) piperidine-1-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.58 (s, 1H), 8.34 (s, 1H), 7.95 (s, 1H), 7.42-7.33 (m, 5H), 7.31 -7.17 (m, 3H), 7.00 (q, J = 8.5 Hz, 2H), 6.59-6.50 (m, 1H), 5.68-5.60 (m, 1H), 4.86-4.73 (m, 1H), 4.10 (d , J = 13.3 Hz, 2H), 3.60 (s, 2H), 2.96 (t, J = 12.6 Hz, 2H), 2.18 (t, J = 7.4 Hz, 1H), 0.86-0.78 (m, 6H).

MS (ESI +) m / z 549 (M + H) ⁺

Example  502: N- (4- (4-((2S) -1- (3,5-) Difluorobenzoyl )-2- Methylpiperidine 4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] -cyclopropanecarboxamide (N- (4- (4-(((2S) -1- (3,5-difluorobenzoyl) ) -2-methylpiperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 530 (M + H) ⁺

Example  503: N- (4- (4-(((2S) -1- (2- Fluoroisonicotinoyl )-2- Methylpiperidine -4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((2S) -1--1- ( Synthesis of 2-fluoroisonicotinoyl) -2-methylpiperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 513 (M + H) ⁺

Example  504: (2S) -4-((4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl) amino) -2-methyl-N -(2,2,2-trifluoroethyl) piperidine-1-carboxamide ((2S) -4-((4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3-b] pyridin Synthesis of -4-yl) phenyl) amino) -2-methyl-N- (2,2,2-trifluoroethyl) piperidine-1-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (s, 1H), 10.53 (s, 1H), 7.94 (s, 1H), 7.54-7.47 (m, 2H), 7.33 (dd, J = 3.5, 2.5Hz, 1H), 6.75 (dd, J = 8.9, 3.1Hz, 2H), 6.55 (td, J = 3.4, 1.9Hz, 1H), 3.93-3.77 (m, 3H), 3.59 (d, J = 2.8 Hz, 1H), 2.05-2.00 (m, 1H), 1.95-1.80 (m, 2H), 1.66 (dd, J = 30.6, 12.3 Hz, 2H), 1.23 (s, 2H), 1.17 (d, J = 6.7 Hz, 2H), 0.83-0.77 (m, 4H).

MS (ESI +) m / z 515 (M + H) ⁺

Example  505: 4-((4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -2-fluorophenyl) amino) -N- (2 , 2,2-trifluoroethyl) piperidine-1-carboxamide (4-((4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3-b] pyridin -4- yl ) -2-fluorophenyl) amino) -N- (2,2,2-trifluoroethyl) piperidine-1-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.47 (s, 1H), 10.58 (s, 1H), 7.95 (s, 1H), 7.40-7.34 (m, 3H), 7.17 (t, J = 6 Hz, 1H), 6.99 (t, J = 8.8 Hz, 1H), 6.55 (m, 1H), 5.63 (d, J = 8.4, 1H), 4.02 (d, J = 13.6 Hz, 2H), 3.87 (m, 2H ), 3.57 (m, 1H), 2.90 (t, J = 12.4 Hz, 2H), 2.03 (m, 1H), 1.91 (d, J = 10.8 Hz, 2H), 1.42 (m, 2H), 0.84 (m , 4H).

MS (ESI +) m / z 519 (M + H) ⁺

Example  506: (2S) -4-((4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) amino) -N- (2,4-difluorophenyl) -2-methylpiperidine-1-carboxamide ((2S) -4-((4- (6- ( Synthesis of cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl) amino) -N- (2,4-difluorophenyl) -2-methylpiperidine-1-carboxamide)

MS (ESI +) m / z 545 (M + H) ⁺

Example  507: N- (4- (4-((1- Isicotinoylpiperidine -4-yl) amino) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((1-isonicotinoylpiperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

MS (ESI +) m / z 481 (M + H) ⁺

Example  508: N- (4- (4-((1- (3,5- Difluorobenzoyl ) Piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- ( Synthesis of 3,5-difluorobenzoyl) piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.40 (s, 1H), 10.52 (s, 1H), 7.94 (d, J = 7.9 Hz, 1H), 7.56 -7.30 (m, 4H), 7.17 ( dt, J = 5.8, 2.2 Hz, 2H), 6.82-6.70 (m, 2H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 5.94 (d, J = 7.7 Hz, 1H), 4.32 (d , J = 13.3 Hz, 1H), 3.69-3.49 (m, 3H), 3.16 (d, J = 46.7 Hz, 3H), 2.03 (s, 2H), 1.91 (s, 1H), 0.82-0.73 (m, 4H).

MS (ESI +) m / z 516 (M + H) ⁺

Example  509: N- (4- (4-((1- (2- Fluoroisonicotinoyl ) Piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- ( Synthesis of 2-fluoroisonicotinoyl) piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.40 (s, 1H), 10.52 (s, 1H), 8.35 (d, J = 5.0 Hz, 1H), 7.93 (s, 1H), 7.53-7.45 ( m, 2H), 7.37 (dt, J = 4.9, 1.8 Hz, 1H), 7.33 (dd, J = 3.5, 2.5 Hz, 1H), 7.26 (t, J = 1.5 Hz, 1H), 6.80-6.73 (m , 2H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 5.96 (d, J = 7.8 Hz, 1H), 4.33 (d, J = 13.2 Hz, 1H), 3.63 (s, 1H), 3.47 (d, J = 13.9 Hz, 1H), 3.22 (t, J = 12.0 Hz, 1H), 3.13 (t, J = 11.5 Hz, 1H), 2.06 (d, J = 15.0 Hz, 2H), 1.93 (s , 1H), 1.50-1.31 (m, 2H), 0.79 (m, 4H).

MS (ESI +) m / z 499 (M + H) ⁺

Example  510: N- (4- (4-((1- (3,5- Difluorobenzoyl ) Azetidine -3-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- (3,5- Synthesis of difluorobenzoyl) azetidin-3-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.94 (s, 1H), 7.57-7.49 (m, 4H), 7.46 (tt, J = 9.2 , 2.4 Hz, 2H), 7.34 (dt, J = 6.2, 2.1 Hz, 3H), 6.68 (dd, J = 11.8, 7.5 Hz, 3H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 4.72 (t, J = 7.9 Hz, 1H), 4.46 (t, J = 8.8 Hz, 1H), 4.37-4.27 (m, 1H), 4.13 (dd, J = 8.6, 4.9 Hz, 1H), 3.93 (dd, J = 10.4, 5.0 Hz, 1H), 2.03 (s, 1H), 0.82-0.75 (m, 4H).

MS (ESI +) m / z 488 (M + H) ⁺

Example 511: 4 -((4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) amino) -N- (2,4-difluorophenyl) piperidine-1-carboxamide (4-((4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2 , 3-b] pyridin-4-yl) phenyl) amino) -N- (2,4-difluorophenyl) piperidine-1-carboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.40 (s, 1H), 10.53 (s, 1H), 8.94 (d, J = 2.2 Hz, 1H), 8.34 (s, 1H), 8.10 (td, J = 9.2, 6.1 Hz, 1H), 7.94 (d, J = 4.3 Hz, 1H), 7.50 (d, J = 8.6 Hz, 2H), 7.35-7.30 (m, 1H), 7.24 (ddd, J = 10.7 , 9.1, 2.9 Hz, 1H), 7.08-6.93 (m, 1H), 6.76 (d, J = 8.7 Hz, 2H), 6.55 (dd, J = 3.5, 1.9 Hz, 1H), 5.96 (d, J = 8.1 Hz, 1H), 4.03 (d, J = 13.4 Hz, 2H), 3.55 (d, J = 9.8 Hz, 1H), 3.03 (t, J = 11.7 Hz, 2H), 2.11-1.92 (m, 3H) , 1.41-1.31 (m, 2H), 0.85-0.71 (m, 4H).

MS (ESI +) m / z 531 (M + H) ⁺

Example 512: 4 -((4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) amino) -N- (2,2,2-trifluoroethyl) piperidine-1-carboxamide (4-((4- (6- (cyclopropanecarboxamido) -1H-pyrrolo Synthesis of [2,3-b] pyridin-4-yl) phenyl) amino) -N- (2,2,2-trifluoroethyl) piperidine-1-carboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.39 (s, 1H), 10.52 (s, 1H), 7.93 (s, 1H), 7.49 (d, J = 8.6 Hz, 2H), 7.33 (dd, J = 3.5, 2.5 Hz, 1H), 7.16 (t, J = 6.2 Hz, 1H), 6.74 (d, J = 8.5 Hz, 2H), 6.54 (dd, J = 3.5, 1.9 Hz, 1H), 5.92 ( d, J = 8.1 Hz, 1H), 3.93 (d, J = 13.4 Hz, 2H), 3.84 (dtd, J = 16.1, 9.7, 6.5 Hz, 3H), 3.51 (s, 1H), 2.94 (t, J = 12.4 Hz, 2H), 2.05 (d, J = 17.6 Hz, 1H), 1.92 (d, J = 12.2 Hz, 2H), 0.84-0.76 (m, 4H).

MS (ESI +) m / z 501 (M + H) ⁺

Example 513: 3 -((4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) amino) -N- (2,4-difluorophenyl) azetidine-1-carboxamide (3-((4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2, Synthesis of 3-b] pyridin-4-yl) phenyl) amino) -N- (2,4-difluorophenyl) azetidine-1-carboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 8.27 (s, 1H), 7.95 (s, 1H), 7.53 (dq, J = 8.9, 3.1 Hz, 3H), 7.34 (dd, J = 3.5, 2.5 Hz, 1H), 7.26 (ddd, J = 10.8, 9.0, 2.9 Hz, 1H), 7.07-6.97 (m, 1H), 6.69 (d, J = 8.8 Hz, 3H), 6.54 (dd, J = 3.5, 1.9 Hz, 1H), 4.32 (m, 3H), 3.79 (dd, J = 8.2, 4.1 Hz, 2H), 2.03 (s, 1H), 0.84- 0.76 (m, 4 H).

MS (ESI +) m / z 503 (M + H) ⁺

Example 514: 3 -((4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) amino) -N- (2,2,2-trifluoroethyl) azetidine-1-carboxamide (3-((4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [ Synthesis of 2,3-b] pyridin-4-yl) phenyl) amino) -N- (2,2,2-trifluoroethyl) azetidine-1-carboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.95 (d, J = 2.9 Hz, 2H), 7.52 (d, J = 8.6 Hz, 2H) , 7.34 (dd, J = 3.5, 2.5 Hz, 1H), 7.08 (t, J = 6.3 Hz, 1H), 6.67 (d, J = 8.7 Hz, 2H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 4.26-4.22 (m, 2H), 3.86-3.72 (m, 3H), 3.71-3.65 (m, 2H), 2.03 (s, 1H), 0.87-076 (m, 4H).

MS (ESI +) m / z 473 (M + H) ⁺

Example  515: N- (4- (4-((1- (2- Cyanoacetyl ) Azetidine -3-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- (2-cyanoacetyl)) Synthesis of azetidin-3-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 415 (M + H) ⁺

Example  516: N- (4- (4-((1- (2- Cyanoacetyl ) Piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- ( Synthesis of 2-cyanoacetyl) piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 443 (M + H) ⁺

Example  517: N- (4- (4-((1- (3,3,3- Trifluoropropanoyl ) Azetidine -3-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- (3,3, Synthesis of 3-trifluoropropanoyl) azetidin-3-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.42 (s, 1H), 10.54 (s, 1H), 7.95 (s, 1H), 7.53 (d, J = 8.4 Hz, 2H), 7.34 (t, J = 3.0 Hz, 1H), 6.67 (d, J = 8.3 Hz, 3H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 4.55 (t, J = 7.7 Hz, 1H), 4.29 (d, J = 6.2 Hz, 2H), 4.03-3.90 (m, 1H), 3.75 (d, J = 5.3 Hz, 1H), 3.40 (m, 2H), 2.03 (s, 1H), 0.84-0.76 (m, 4H ).

MS (ESI +) m / z 458 (M + H) ⁺

Example  518: N- (4- (4-((1- (3,3,3- Trifluoropropanoyl ) Piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((1- ( Synthesis of 3,3,3-trifluoropropanoyl) piperidin-4-yl) amino) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO- d ₆ ) δ 11.39 (s, 1H), 10.52 (s, 1H), 7.94 (s, 1H), 7.50 (d, J = 8.6 Hz, 2H), 7.33 (dd, J = 3.5, 2.5 Hz, 1H), 6.76 (d, J = 8.6 Hz, 2H), 6.54 (dd, J = 3.5, 1.9 Hz, 1H), 5.95 (d, J = 8.0 Hz, 1H), 4.25 ( d, J = 13.2 Hz, 1H), 3.82 (d, J = 13.8 Hz, 1H), 3.76-3.53 (m, 3H), 3.21 (t, J = 11.9 Hz, 1H), 2.90 (t, J = 11.3 Hz, 1H), 2.05-1.90 (m, 3H), 1.44-1.22 (m, 2H), 0.85-0.76 (m, 4H).

MS (ESI +) m / z 486 (M + H) ⁺

Example  519: N- (4- (4- (2- Cyanoacetyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- cyanoacetyl ) phenyl ) -1H- pyrrolo [2,3- b] pyridin-6-yl) cyclopropanecarboxamide)

N- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1-tosyl-1H-pyrrolo [2, 3-b] pyridin-6-yl) cyclopropanecarboxamide 1.0 g (2.1 mmol) is dissolved in a DMF / H ₂ O = 2: 1 solution and 3- (4-bromophenyl) -3-oxopropane Nitrile 0.6 g (2.5 mmol), Pd (PPh ₃ ) ₄ 0.2 g (0.2 mmol), 0.15 mL of 2M K ₂ CO ₃ aqueous solution was added and stirred at 100 ~ 110 ^° C. for 2 hours. When the reaction was completed, the mixture was cooled to room temperature, water was added, and extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was separated by NH-silica gel column chromatography (n-hexane / ethyl acetate = 5: 1), and N- (4- (4- (2-cyanoacetyl) phenyl) -1-tosyl-1H-pi Rolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide was synthesized. The synthesized material was dissolved in MeOH / THF (1: 1) solution and 2N aqueous sodium hydroxide solution was added and stirred at 30-40 ^° C. for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and saturated aqueous ammonium chloride solution was added with stirring. The resulting solid was filtered to give the product N- (4- (4- (2-cyanoacetyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide It was.

MS (ESI +) m / z 345 (M + H) ⁺

Examples 520-598

Hereinafter, in Examples 520 to 598, the synthesis was carried out in the same manner as in Example 519, or by using a suitable reactant in consideration of the structure of Scheme 1 and the compound to be prepared.

Example  520: N- (4- (4- (1,1- Dioxidothiomorpholine 4-carbonyl) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (1,1-dioxidothiomorpholine-4-carbonyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

MS (ESI +) m / z 439 (M + H) ⁺

Example  521: N- (4- (4- ( Thiomorpholine 4-carbonyl) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( thiomorpholine -4- carbonyl ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.66 (s, 1H), 8.17-8.01 (m, 1H), 7.78 (d, J = 7.7 Hz, 2H), 7.57 ( d, J = 7.7 Hz, 2H), 7.43 (s, 1H), 6.56 (s, 1H), 3.76 (d, J = 100.0 Hz, 6H), 2.76-2.61 (m, 6H), 2.07 (d, J = 13.0 Hz, 1H), 0.80 (d, J = 12.3 Hz, 4H).

MS (ESI +) m / z 407 (M + H) ⁺

Example  522: N- (4- (2- methyl -4- (morpholine-4-carbonyl) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (2- methyl -4-( morpholine Synthesis of -4-carbonyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 405 (M + H) ⁺

Example  523: N- ( Cyanomethyl ) -4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) benzamide (N- ( cyanomethyl ) -4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) benzamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.61 (s, 1H), 10.67 (s, 1H), 9.32 (s, 1H), 8.09 (s, 1H), 8.04 (d, J = 8.0 Hz, 2H), 7.84 (d, J = 8.0 Hz, 2H), 7.44 (d, J = 3.3 Hz, 1H), 6.55 (d, J = 3.4 Hz, 1H), 4.35 (d, J = 5.2 Hz, 2H) , 2.07 (d, J = 12.0 Hz, 1H), 0.87-0.75 (m, 4H).

MS (ESI +) m / z 360 (M + H) ⁺

Example 524: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -N- (2,2,2-trifluoroethyl) benzamide (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) -N- (2,2,2-trifluoroethyl) benzamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.60 (s, 1H), 8.02 (s, 1H), 7.65 (d, J = 8.0 Hz, 2H), 7.42 (dd, J = 5.4, 17.0 Hz, 3H), 6.53 (s, 1H), 3.54-3.47 (m, 2H), 2.02 (dd, J = 7.9, 15.2 Hz, 1H), 0.84-0.77 (m, 4H).

MS (ESI +) m / z 403 (M + H) ⁺

Example 525: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -3-methyl-N- (2,2,2-trifluoroethyl) benzamide (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4- yl) -3-methyl-N- (2,2,2-trifluoroethyl) benzamide)

MS (ESI +) m / z 417 (M + H) ⁺

Example  526: N- ( Cyanomethyl ) -4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3-methylbenzamide (N- ( cyanomethyl ) -4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-methylbenzamide)

MS (ESI +) m / z 374 (M + H) ⁺

Example  527: N- ( Cyanomethyl ) -4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -N, 3-dimethylbenzamide (N- (cyanomethyl) -4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -N, 3- synthesis of dimethylbenzamide)

MS (ESI +) m / z 388 (M + H) ⁺

Example  528: N- ( Cyanomethyl ) -4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -2-fluorobenzamide (N- ( cyanomethyl ) -4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -2-fluorobenzamide)

MS (ESI +) m / z 378 (M + H) ⁺

Example  529: N- ( Cyanomethyl ) -4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -2,6-difluorobenzamide (N- (cyanomethyl) -4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -2, 6-difluorobenzamide)

MS (ESI +) m / z 396 (M + H) ⁺

Example  530: N- ( Cyanomethyl ) -4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) cyclohex-3-ene-1-carboxamide (N- (cyanomethyl) -4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) cyclohex Synthesis of -3-ene-1-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.49 (s, 1H), 8.62 (t, J = 5.6 Hz, 1H), 7.83 (s, 1H), 7.31 (dd, J = 3.5, 2.5 Hz, 1H), 6.50 (dd, J = 3.6, 1.8 Hz, 1H), 6.31 (s, 1H), 4.16 (d, J = 5.6 Hz, 2H), 2.40 (s, 2H), 2.00 (d, J = 12.1 Hz, 2H), 1.72 (ddt, J = 17.9, 12.1, 6.3 Hz, 1H), 0.79 (ddt, J = 13.1, 5.1, 3.0 Hz, 4H)

MS (ESI +) m / z 364 (M + H) ⁺

Example 531: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -N- (2,2,2-trifluoroethyl) cyclohex-3-ene-1-carboxamide (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3- b] Synthesis of pyridin-4-yl) -N- (2,2,2-trifluoroethyl) cyclohex-3-ene-1-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.49 (s, 1H), 8.55 (t, J = 6.4 Hz, 1H), 7.83 (s, 1H), 7.31 (dd, J = 3.5, 2.4 Hz, 1H), 6.49 (dd, J = 3.6, 1.9 Hz, 1H), 6.32 (d, J = 4.0 Hz, 1H), 3.94 (ddt, J = 11.6, 9.1, 4.9 Hz, 2H ), 2.62-2.54 (m, 2H), 2.39 (d, J = 6.7 Hz, 2H), 2.05-1.95 (m, 3H), 1.73 (ddt, J = 17.9, 12.1, 6.3 Hz, 1H), 0.87- 0.72 (m, 4H)

MS (ESI +) m / z 407 (M + H) ⁺

Example  532: N- (2- Cyanoethyl ) -4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) cyclohex-3-ene-1-carboxamide (N- (2-cyanoethyl) -4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl Synthesis of Cyclohex-3-ene-1-carboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.37 (s, 1H), 10.49 (s, 1H), 8.27 (t, J = 5.8 Hz, 1H), 7.83 (s, 1H), 7.38-7.27 ( m, 1H), 6.50 (dd, J = 3.6, 1.9 Hz, 1H), 6.31 (s, 1H), 2.67 (t, J = 6.5 Hz, 2H), 2.56-2.43 (m, 3H) 2.38 (d, J = 6.0 Hz, 2H), 2.06-1.93 (m, 3H), 1.79-1.67 (m, 1H), 0.85 (t, J = 6.4 Hz, 1H), 0.79 (ddt, J = 10.1, 5.0, 2.6 Hz , 4H).

MS (ESI +) m / z 378 (M + H) ⁺

Example  533: N- (4- (4-((N- Methylsulfamoyl ) methyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((N- methylsulfamoyl ) methyl ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.57 (s, 1H), 10.66 (s, 1H), 8.05 (d, J = 4.7 Hz, 1H), 7.73 (d, J = 7.9 Hz, 2H) , 7.54 (d, J = 7.9 Hz, 2H), 7.42 (t, J = 3.1 Hz, 1H), 7.04-6.94 (m, 1H), 6.54 (dd, J = 3.7, 1.8 Hz, 1H), 4.42 ( s, 2H), 2.62 (d, J = 4.7 Hz, 3H), 2.07-2.00 (m, 1H), 0.85-0.72 (m, 4H)

MS (ESI +) m / z 385 (M + H) ⁺

Example  534: N- (4- (4-(( Morpholinosulfonyl ) methyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine Synthesis of -6-yl) cyclopropanecarboxamide (N- (4- (4-((morpholinosulfonyl) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.58 (s, 1H), 10.66 (s, 1H), 8.06 (s, 1H), 7.75 (d, J = 7.8 Hz, 2H), 7.59 (d, J = 7.8 Hz, 2H), 7.43 (s, 1H), 6.54 (s, 1H), 4.54 (s, 2H), 3.61 (s, 4H), 3.15 (d, J = 5.8 Hz, 4H), 2.05 ( s, 1 H), 0.86-0.75 (m, 4 H).

MS (ESI +) m / z 441 (M + H) ⁺

Example  535: N- (4- (4- (2- (1,1- Deoxythiomorpholino )-2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (1,1-dioxidothiomorpholino) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (s, 1H), 8.03 (s, 1H), 7.67 (d, J = 7.8 Hz, 2H), 7.56 (s, 1H), 7.41 (d, J = 6.9 Hz, 2H), 6.54 (s, 1H), 3.94-3.88 (m, 4H), 3.16 (d, J = 21.7 Hz, 4H), 2.05 (s, 1H), 0.89-0.76 (m, 4H)

MS (ESI +) m / z 453 (M + H) ⁺

Example  536: N- (4- (4- (2- Morpholino -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyrid Din-6-yl) cyclopropanecarboxamide (N- (4- (4- (2-morpholino-2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (s, 1H), 8.03 (s, 1H), 7.67 (d, J = 7.7 Hz, 2H), 7.39 (d, J = 7.5 Hz, 2H), 6.54 (s, 1H), 3.81 (s, 2H), 3.53 (s, 6H), 3.48 (s, 2H), 2.05 (s, 1H), 0.88-0.77 (m, 4H ).

MS (ESI +) m / z 405 (M + H) ⁺

Example  537: N- (4- (4- (2-oxo-2-((2,2,2- Trifluoroethyl ) Amino) ethyl) phenyl) -1Hpyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2-oxo-2-((2,2,2)) , 2-trifluoroethyl) amino) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.63 (s, 1H), 8.83 (s, 1H), 8.02 (s, 1H), 7.66 (d, J = 7.7 Hz, 2H), 7.59-7.54 (m, 1H), 7.42 (t, J = 7.1 Hz, 2H), 6.53 (s, 1H), 4.00-3.91 (m, 2H), 3.61 (s, 2H), 2.05 (s , 1H), 0.87-0.76 (m, 4H).

MS (ESI +) m / z 417 (M + H) ⁺

Example  538: N- (4- (4- (2-((1,1- Deoxytetrahydrothiophene -3-yl) amino) -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2-((1,1-dioxidotetrahydrothiophen-3-yl) Synthesis of amino) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 453 (M + H) ⁺

Example  539: N- (4- (4- (2- ( Methylamino )-2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- ( methylamino ) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.03 (d, J = 8.0 Hz, 2H), 7.69-7.60 (m, 2H), 7.47- 7.36 (m, 3H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 3.47 (s, 3H), 2.60 (d, J = 4.6 Hz, 2H), 2.08-1.98 (m, 1H), 0.83 0.73 (m, 4 H).

MS (ESI +) m / z 349 (M + H) ⁺

Example  540: N- (4- (4- (2- (dimethylamino) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- ( dimethylamino ) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.71-7.62 (m, 2H), 7.43-7.35 (m, 3H ), 6.54 (dd, J = 3.5, 1.8 Hz, 1H), 3.77 (s, 2H), 3.04 (s, 3H), 2.85 (s, 3H), 2.03 (d, J = 8.1 Hz, 1H), 0.83 0.76 (m, 4 H).

MS (ESI +) m / z 363 (M + H) ⁺

Example  541: N- (4- (4- (2- ( Ethylamino )-2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- ( ethylamino ) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.11 (t, J = 5.2 Hz, 1H), 8.02 (s, 1H), 7.72-7.59 ( m, 2H), 7.49-7.31 (m, 4H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 3.45 (s, 2H), 3.08 (qd, J = 7.2, 5.4 Hz, 2H), 2.09 1.98 (m, 1H), 1.03 (t, J = 7.2 Hz, 3H), 0.85-0.72 (m, 4H).

MS (ESI +) m / z 363 (M + H) ⁺

Example  542: N- (4- (4- (2- (4- ( Methylsulfonyl Piperazin-1-yl) -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4- (methylsulfonyl) piperazin-1-yl) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.64 (s, 1H), 8.03 (s, 1H), 7.67 (d, J = 8.1 Hz, 2H), 7.46-7.36 ( m, 3H), 6.54 (dd, J = 3.5, 1.9 Hz, 1H), 3.84 (s, 2H), 3.66 (s, 4H), 3.09 (d, J = 5.3 Hz, 4H), 2.88 (s, 3H ), 2.09-1.99 (m, 1H), 0.84-0.73 (m, 4H).

MS (ESI +) m / z 482 (M + H) ⁺

Example  543: N- (4- (4- (2- (4- Acetylpiperazine -1-yl) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4-acetylpiperazin-1-yl) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 446 (M + H) ⁺

Example  544: N- (4- (4- (2- ( Ixoxazole -3- Monoamino )-2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (isoxazol-3-ylamino) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 8.23 (d, J = 1.7 Hz, 1H), 8.01 (s, 1H), 7.70 (d, J = 7.8 Hz, 2H), 7.42 (d, J = 7.8 Hz, 2H), 7.20 (d, J = 3.5 Hz, 1H), 7.01 (s, 1H), 6.58 (s, 1H), 3.75 (s, 2H), 2.19-2.10 (m, 1H), 1.97 (d , J = 12.6 Hz, 1H), 0.83-0.80 (m, 4H).

MS (ESI +) m / z 402 (M + H) ⁺

Example  545: N- (4- (4- (2- (1,1- Deoxythiomorpholino )-2- Oxoethyl )-2- Methylphenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (1,1-dioxidothiomorpholino) -2-oxoethyl) -2 -methylphenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 467 (M + H) ⁺

Example  546: N- (4- (4- (2- ( Azetidine -1-yl) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- ( azetidin -One- yl ) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.71-7.62 (m, 2H), 7.42-7.36 (m, 3H ), 6.54 (dd, J = 3.5, 1.7 Hz, 1H), 4.21 (t, J = 7.7 Hz, 2H), 3.84 (dt, J = 16.3, 8.0 Hz, 2H), 3.48 (s, 6H), 2.19 (p, J = 7.7 Hz, 1H), 2.01 (dd, J = 14.7, 7.3 Hz, 3H), 0.85-0.71 (m, 4H).

MS (ESI +) m / z 375 (M + H) ⁺

Example  547: N- (4- (4- (2-oxo-2- ( Pyrrolidine -1-yl) ethyl) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- oxo -2-( pyrrolidin -1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.70-7.62 (m, 2H), 7.43-7.37 (m, 3H ), 6.54 (dd, J = 3.5, 1.9 Hz, 1H), 3.70 (s, 2H), 3.51 (t, J = 6.8 Hz, 2H), 3.31 (t, J = 6.8 Hz, 2H), 2.07-1.97 (m, 1H), 1.89 (p, J = 6.8 Hz, 2H), 1.77 (p, J = 6.8 Hz, 2H), 0.84-0.74 (m, 4H).

MS (ESI +) m / z 389 (M + H) ⁺

Example  548: N- (4- (4- (2- (4- Cyanopiperidine -1-yl) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4-cyanopiperidin-1-yl) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.71-7.63 (m, 2H), 7.44-7.36 (m, 3H ), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 3.89-3.78 (m, 3H), 3.08 (s, 1H), 2.07-1.94 (m, 2H), 1.90-1.77 (m, 2H), 1.60 (ddt, J = 12.8, 8.9, 4.7 Hz, 2H), 0.83-0.75 (m, 4H).

MS (ESI +) m / z 428 (M + H) ⁺

Example  549: N- (4- (4- (2-oxo-2- (4- Oxopiperidine -1-yl) ethyl) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2-oxo-2- (4-oxopiperidin-1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] Synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.67 (d, J = 7.9 Hz, 2H), 7.46-7.37 ( m, 3H), 6.54 (dd, J = 3.6, 1.9 Hz, 1H), 3.90 (s, 2H), 3.86-3.73 (m, 4H), 2.36 (q, J = 5.5, 4.8 Hz, 2H), 2.06 1.96 (m, 2H), 1.15 (d, J = 6.6 Hz, 2H), 0.80 (m, 4H).

MS (ESI +) m / z 417 (M + H) ⁺

Example  550: N- (4- (4- (2- (4- Methylpiperazine -1-yl) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4-methylpiperazin-1-yl) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.03 (s, 1H), 7.71-7.63 (m, 2H), 7.42-7.36 (m, 3H ), 6.53 (dd, J = 3.5, 1.8 Hz, 1H), 3.79 (s, 2H), 3.55-3.44 (m, 4H), 2.24 (q, J = 4.6 Hz, 4H), 2.15 (s, 3H) , 2.08-1.98 (m, 1 H), 0.80 (m, 4 H).

MS (ESI +) m / z 418 (M + H) ⁺

Example  551: N- (4- (4- (2- (4- Ethyl piperazine -1-yl) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4-ethylpiperazin-1-yl) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.03 (s, 1H), 7.70-7.63 (m, 2H), 7.43-7.37 (m, 3H ), 6.56-6.50 (m, 1H), 3.79 (s, 2H), 3.55-3.44 (m, 4H), 2.29 (td, J = 8.4, 7.8, 5.2 Hz, 6H), 2.04-1.96 (m, 1H ), 0.98 (t, J = 6.8 Hz, 3H), 0.83-0.71 (m, 4H).

MS (ESI +) m / z 432 (M + H) ⁺

Example  552: N- (4- (4- (2- (4- Isopropylpiperazine -1-yl) -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4-isopropylpiperazin-1-yl) -2- oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.70-7.62 (m, 2H), 7.49-7.44 (m, 1H ), 7.42-7.35 (m, 3H), 7.11 (d, J = 7.8 Hz, 1H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 3.79 (s, 2H), 3.55-3.43 (m, 4H), 2.63 (d, J = 6.5 Hz, 1H), 2.37 (d, J = 9.1 Hz, 4H), 2.05-1.95 (m, 1H), 0.94 (d, J = 6.5 Hz, 6H), 0.81 ( qd, J = 9.0, 7.8, 4.5 Hz, 4H).

MS (ESI +) m / z 446 (M + H) ⁺

Example  553: N- (4- (4- (2-((2- Cyanoethyl ) Amino) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2-((2-cyanoethyl) amino) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin- Synthesis of 6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.65 (d, J = 8.1 Hz, 2H), 7.49-7.36 ( m, 3H), 6.53 (dd, J = 3.5, 1.8 Hz, 1H), 3.53 (s, 2H), 3.31 (m, 2H), 2.66 (m, 2H), 2.07-1.96 (m, 1H), 0.82 (m, 4 H).

MS (ESI +) m / z 388 (M + H) ⁺

Example  554: tert - Butyl 4 -(2- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) acetyl) piperazine-1-carboxylate ( tert - butyl  Synthesis of 4- (2- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl) acetyl) piperazine-1-carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (d, J = 2.6 Hz, 1H), 10.63 (s, 1H), 8.03 (s, 1H), 7.72-7.63 (m, 2H), 7.44- 7.35 (m, 3H), 6.54 (dd, J = 3.6, 1.9 Hz, 1H), 3.82 (s, 2H), 3.58-3.43 (m, 4H), 3.32-3.24 (m, 4H), 2.07-1.94 ( m, 1H), 1.40 (s, 9H), 0.87-0.74 (m, 4H).

MS (ESI +) m / z 504 (M + H) ⁺

Example  555: tert - Butyl 3 -(2- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) acetamide) piperidine-1-carboxylate ( tert - butyl  Synthesis of 3- (2- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl) acetamido) piperidine-1-carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.63 (s, 1H), 8.11 (d, J = 7.5 Hz, 1H), 8.02 (s, 1H), 7.65 (d, J = 8.1 Hz, 2H), 7.46-7.37 (m, 3H), 6.53 (dd, J = 3.4, 1.8 Hz, 1H), 3.64-3.53 (m, 2H), 3.50 (s, 3H), 2.00 (dt , J = 14.5, 6.7 Hz, 2H), 1.85-1.76 (m, 1H), 1.73-1.61 (m, 1H), 1.37 (s, 13H), 1.23 (s, 5H), 0.88-0.72 (m, 6H ).

MS (ESI +) m / z 518 (M + H) ⁺

Example  556: N- (4- (4- (2-((1- methyl -1H- Pyrazole -3-yl) amino) -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2-((1-methyl-1H-pyrazol-3- Synthesis of yl) amino) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.68 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.67 (d, J = 8.1 Hz, 2H), 7.53 (d, J = 2.2 Hz, 1H), 7.48 (d, J = 8.0 Hz, 2H), 7.40 (dd, J = 3.5, 2.4 Hz, 1H), 6.54 (dd, J = 3.5, 1.9 Hz, 1H), 6.42 (d, J = 2.2 Hz, 1H), 3.73 (s, 3H), 3.68 (s, 2H), 2.02 (m, 1H), 0.84-0.73 (m, 4H).

MS (ESI +) m / z 415 (M + H) ⁺

Example  557: N- (4- (4- (2-oxo-2- (piperidin-1-yl) ethyl) phenyl) -1 H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- oxo -2-( piperidin -1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.60 (d, J = 3.9 Hz, 1H), 8.03 (d, J = 3.2 Hz, 1H), 7.67 (d, J = 6.8 Hz, 2H), 7.40 (s, 3H), 6.53 (s, 1H), 3.78 (s, 2H), 3.60 (s, 2H), 3.46 (s, 2H), 2.04 (s, 1H), 1.75 ( d, J = 4.4 Hz, 2H), 1.55 (s, 2H), 1.41 (s, 2H), 0.82-0.75 (m, 4H).

MS (ESI +) m / z 403 (M + H) ⁺

Example  558: N- (4- (4- (2-oxo-2- (piperazin-1-yl) ethyl) phenyl) -1 H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- oxo -2-( piperazin -1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, CDCl 3) δ 8.05 (s, 1H), 7.69 (dd, J = 8.2, 3.9 Hz, 2H), 7.36-7.29 (m, 2H), 7.20 (q, J = 3.1 Hz, 1H ), 6.57 (q, J = 3.1 Hz, 1H), 5.34-5.24 (m, 2H), 3.84-3.73 (m, 2H), 3.63 (d, J = 5.2 Hz, 2H), 3.45 (d, J = 5.3 Hz, 2H), 2.81 (s, 2H), 2.67 (d, J = 5.3 Hz, 2H), 1.65 (s, 1H), 1.07 (q, J = 3.9 Hz, 2H), 0.85 (m, 2H) .

MS (ESI +) m / z 404 (M + H) ⁺

Example  559: N- (4- (4- (2- (1,1- Deoxythiomorpholino )-2- Oxoethyl ) -3- Fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (1,1-dioxidothiomorpholino) -2-oxoethyl) -3 -fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 471 (M + H) ⁺

Example  560: N- (4- (4- (2-oxo-2- Thiomorpholinoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2-oxo-2-thiomorpholinoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

MS (ESI +) m / z 421 (M + H) ⁺

Example  561: N- (4- (4- (2- (4,4- Difluoropiperidine -1-yl) -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4,4-difluoropiperidin-1-yl)- Synthesis of 2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 439 (M + H) ⁺

Example  562: N- (4- (4- (2-oxo-2- (4- ( Trifluoromethylsulfonyl ) Piperazin-1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2-oxo-2 Synthesis of-(4- (trifluoromethylsulfonyl) piperazin-1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 8.01 (s, 1H), 7.65 (d, J = 8.0 Hz, 2H), 7.43-7.31 ( m, 3H), 6.52 (dd, J = 3.5, 1.9 Hz, 1H), 4.33 (d, J = 4.3 Hz, 1H), 3.77 (s, 2H), 2.60 (dd, J = 12.1, 5.3 Hz, 8H ), 2.00 (m, 1 H), 0.84-0.76 (m, 4 H).

MS (ESI +) m / z 537 (M + H) ⁺

Example  563: N- (4- (4- (2- (4- ( Ethylsulfonyl Piperazin-1-yl) -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4- (ethylsulfonyl) piperazin-1-yl) Synthesis of -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (s, 1H), 8.03 (s, 1H), 7.67 (d, J = 8.0 Hz, 2H), 7.40 (d, J = 7.6 Hz, 3H), 6.53 (d, J = 3.4 Hz, 1H), 3.84 (s, 2H), 3.64 3.57 (m, 2H), 3.20-3.10 (m, 4H), 3.11-2.99 (m, 4H), 2.07-1.95 (m, 1H), 1.24-1.14 (m, 3H), 0.82 (dd, J = 16.1, 11.1 Hz, 4H).

MS (ESI +) m / z 497 (M + H) ⁺

Example  564: N- (4- (4- (2-oxo-2- (4- ( Propylsulfonyl ) Piperazin-1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2-oxo-2 Synthesis of-(4- (propylsulfonyl) piperazin-1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.61 (s, 1H), 8.03 (s, 1H), 7.67 (d, J = 8.0 Hz, 2H), 7.40 (dd, J = 6.2, 2.1 Hz, 3H), 6.54 (dd, J = 3.5, 1.9 Hz, 1H), 3.84 (s, 2H), 3.68-3.54 (m, 4H), 3.14 (m, 4H), 3.08-2.99 (m, 2H), 2.04-1.97 (m, 1H), 1.75-1.60 (m, 2H), 0.95 (t, J = 7.4 Hz, 3H), 0.85-0.74 (m, 4H).

MS (ESI +) m / z 511 (M + H) ⁺

Example  565: ethyl 4- (2- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl) acetyl) piperazine-1-carboxylate ( ethyl  Synthesis of 4- (2- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl) acetyl) piperazine-1-carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (s, 1H), 8.03 (s, 1H), 7.66 (d, J = 7.8 Hz, 2H), 7.45-7.35 ( m, 3H), 6.54 (dd, J = 3.5, 1.8 Hz, 1H), 4.05 (q, J = 7.0 Hz, 2H), 3.83 (s, 2H), 3.58-3.44 (m, 4H), 2.07-1.96 (m, 1H), 1.18 (t, J = 6.9 Hz, 3H), 0.85-0.75 (m, 4H).

MS (ESI +) m / z 477 (M + H) ⁺

Example  566: N- (4- (4- (2- (2-oxo-2- (4- (N- (2,2,2- Trifluoroethyl ) Sulfa Mole ) Piperazin-1-yl) ethyl) phenyl) -1H-pyrrolo [2,3 b] pyridin-6-yl) Cyclopropanecarboxamide  (N- (4- (4- (2- oxo -2- (4- (N- (2,2,2- trifluoroethyl ) sulfamoyl ) piperazin -1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 565 (M + H) ⁺

Example  567: N- (4- (4- (2- (3- Cyanopyrrolidine -1-yl) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (3-cyanopyrrolidin-1-yl) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 414 (M + H) ⁺

Example  568: N- (4- (4- (2- (3- Cyanoazetidine -1-yl) -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (3-cyanoazetidin-1-yl) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 400 (M + H) ⁺

Example  569: N- (4- (4- (2- (3,3- Difluoropyrrolidine -1-yl) -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (3,3-difluoropyrrolidin-1-yl)- Synthesis of 2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (d, J = 4.0 Hz, 1H), 10.60 (d, J = 3.6 Hz, 1H), 8.02 (d, J = 3.4 Hz, 1H), 7.66 (d, J = 6.0 Hz, 2H), 7.40 (s, 3H), 6.54 (s, 1H), 4.11-3.98 (m, 1H), 3.78 (dd, J = 25.2, 10.0 Hz, 5H), 3.55 ( s, 2H), 2.03 (s, 1H), 0.82-0.75 (s, 4H).

MS (ESI +) m / z 425 (M + H) ⁺

Example  570: N- (4- (4- (2-oxo-2- (4- ( Trifluoromethyl ) Piperidin-1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2-oxo- Synthesis of 2- (4- (trifluoromethyl) piperidin-1-yl) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (d, J = 2.9 Hz, 1H), 8.02 (d, J = 2.8 Hz, 1H), 7.66 (t, J = 6.1 Hz, 2H), 7.40 (d, J = 4.1 Hz, 3H), 6.52 (s, 1H), 4.56-4.47 (m, 1H), 4.09 (d, J = 13.9 Hz, 1H), 3.85-3.79 ( m, 2H), 3.06 (t, J = 13.5 Hz, 1H), 2.58 (d, J = 12.3 Hz, 2H), 2.03 (s, 1H), 1.87-1.73 (m, 2H), 1.25 (d, J = 13.1 Hz, 2H), 0.82-0.75 (m, 4H).

MS (ESI +) m / z 471 (M + H) ⁺

Example  571: N- (4- (4- (2- (1,1- Deoxythiomorpholino ) -1,1- Difluoro -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (1,1-dioxidothiomorpholino) -1,1- Synthesis of difluoro-2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 489 (M + H) ⁺

Example  572: N- (4- (4- (1,1- Difluoro -2- Morpholino -2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (1,1-difluoro-2-morpholino-2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

MS (ESI +) m / z 441 (M + H) ⁺

Example  573: N- (4- (4- (2-(( Cyanomethyl ) ( methyl ) Amino) -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2-((cyanomethyl) (methyl) amino) -2-) oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.67 (s, 1H), 8.00 (s, 1H), 7.68 (d, J = 8.1 Hz, 2H), 7.43-7.37 ( m, 3H), 6.55 (dd, J = 3.6, 1.9 Hz, 1H), 4.43 (s, 2H), 3.88 (s, 3H), 3.15 (s, 3H), 2.06-2.02 (m, 1H), 0.85 0.80 (m, 4H).

MS (ESI +) m / z 388 (M + H) ⁺

Example  574: N- (4- (4- (2- (1- Oxothiomorpholine )-2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (1-oxidothiomorpholino) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.65 (s, 1H), 8.02 (s, 1H), 7.68 (d, J = 7.9 Hz, 2H), 7.44-7.38 ( m, 3H), 6.55 (dd, J = 3.5, 1.9 Hz, 1H), 3.87 (d, J = 11.3 Hz, 2H), 3.62 (dd, J = 6.6, 3.9 Hz, 4H), 3.13 (tt, J = 7.4, 3.7 Hz, 4H), 2.04 (d, J = 6.5 Hz, 1H), 0.85-0.79 (m, 4H).

MS (ESI +) m / z 437 (M + H) ⁺

Example  575: N- (4- (4- (2- (4- Cyanopiperidine -1-yl) -1,1- Difluoro -2- Oxoethyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (4-cyanopiperidin-1-yl) -1, 1-difluoro-2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI < + >) m / z 464 (M + H) ⁺

Example  576: N- (4- (4- (2- (3- Cyano morpholino )-2- Oxoethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (3-cyanomorpholino) -2-oxoethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (s, 1H), 8.04 (s, 1H), 7.71-7.66 (m, 2H), 7.45-7.36 (m, 3H ), 6.54 (dd, J = 3.5, 1.8 Hz, 1H), 4.03 (d, J = 12.3 Hz, 2H), 3.94-3.90 (m, 2H), 3.62-3.56 (m, 1H), 3.46 (s, 1H), 2.04 (d, J = 9.1 Hz, 1H), 1.28-1.23 (m, 4H), 0.86-0.79 (m, 4H).

MS (ESI +) m / z 430 (M + H) ⁺

Example  577: N- (4- (4- (1- (1,1- Dioxidothiomorpholine -4-carbonyl) Cyclopropyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (1- (1,1-dioxidothiomorpholine-4-carbonyl) cyclopropyl ) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.62 (s, 1H), 8.03 (s, 1H), 7.70 (dd, J = 7.6, 5.9 Hz, 3H), 7.42- 7.40 (m, 1H), 7.34 (d, J = 8.3 Hz, 2H), 6.53 (dd, J = 3.5, 1.9 Hz, 1H), 3.39 (s, 2H), 2.92 (s, 2H), 2.04-2.00 (m, 1H), 1.51-1.47 (m, 2H), 1.26 (dd, J = 9.2, 4.0 Hz, 4H), 0.84-0.77 (m, 4H).

MS (ESI +) m / z 479 (M + H) ⁺

Example  578: N- (4- (1- (2- (1,1-dioxydothiomorpholino) -2-oxoethyl) -1,2,3,6-tetrahydropyridin-4-yl)- 1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (2- (1,1-dioxidothiomorpholino) -2-oxoethyl) -1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.40 (s, 1H), 10.51 (s, 1H), 7.86 (s, 1H), 7.37-7.28 (m, 1H), 6.60-6.52 (m, 1H) , 6.33 (s, 1H), 3.99 (s, 2H), 3.89 (s, 2H), 3.39 (s, 2H), 3.19 (d, J = 37.2 Hz, 5H), 2.74 (t, J = 5.6 Hz, 2H), 2.00 (d, J = 11.4 Hz, 1H), 0.88-0.75 (m, 4H).

MS (ESI +) m / z 458 (M + H) ⁺

Example  579: N- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) benzyl) morpholine-4-carboxamide (N- (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) benzyl) morpholine-4-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (s, 1H), 8.01 (s, 1H), 7.66 (d, J = 8.3 Hz, 2H), 7.42 (d, J = 8.4 Hz, 3H), 7.21 (s, 1H), 6.53 (s, 1H), 4.32 (s, 2H), 2.42-2.83 (m, 4H), 1.98-2.12 (m, 1H), 1.21-1.41 (m, 4H), 0.72-0.95 (m, 4H).

MS (ESI +) m / z 420 (M + H) ⁺

Example  580: N- (4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) benzyl) thiomorpholine-4-carboxamide 1,1-dioxide (N- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl ) benzyl) thiomorpholine-4-carboxamide 1,1- dioxide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.67 (d, J = 8.0 Hz, 2H), 7.51 (d, J = 5.1 Hz, 1H), 7.44 (d, J = 7.9 Hz, 2H), 7.42-7.38 (m, 1H), 6.58-6.49 (m, 1H), 4.34 (d, J = 5.8 Hz, 2H), 3.82 (d, J = 5.5 Hz, 4H), 3.16-3.06 (m, 4H), 2.04 (s, 1H), 0.80 (dd, J = 4.0, 12.0 Hz, 4H).

MS (ESI +) m / z 468 (M + H) ⁺

Example  581: N- (4- (4-((3- (2,2,2- Trifluoroethyl ) Ureido ) methyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-((3- (2,2,2-trifluoroethyl) ureido) Synthesis of methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.54 (s, 1H), 10.63 (s, 1H), 8.02 (s, 1H), 7.67 (d, J = 7.8 Hz, 2H), 7.45-7.34 ( m, 3H), 6.75 (t, J = 6.0 Hz, 1H), 6.66 (t, J = 6.6 Hz, 1H), 6.55-6.47 (m, 1H), 4.32 (d, J = 6.0 Hz, 2H), 3.93-3.78 (m, 2H), 2.04 (s, 1H), 0.81 (dt, J = 5.3, 10.2 Hz, 4H).

MS (ESI +) m / z 432 (M + H) ⁺

Example  582: N- (4- (4-(((3,4- Difluorophenyl ) Sulfonamido ) methyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-(((3,4-difluorophenyl) sulfonamido) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.61 (s, 1H), 8.24 (br s, 1H), 7.99 (s, 1H), 7.79 (d, J = 2.3 Hz , 1H), 7.69-7.58 (m, 4H), 7.44-7.33 (m, 3H), 6.52-6.43 (m, 1H), 4.13 (s, 2H), 2.04 (d, J = 5.7 Hz, 1H), 0.88-0.74 (m, 4H).

MS (ESI +) m / z 483 (M + H) ⁺

Example  583: N- (4- (4- ( Propylsulfonyl amidomethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( propylsulfonamidomethyl ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.56 (s, 1H), 10.64 (s, 1H), 8.05 (d, J = 15.8 Hz, 1H), 7.79-7.65 (m, 3H), 7.52 ( d, J = 8.1 Hz, 2H), 7.41 (s, 1H), 6.52 (s, 1H), 4.22 (d, J = 4.7 Hz, 2H), 3.02-2.91 (m, 2H), 2.05 (s, 1H ), 1.72-1.59 (m, 2H), 0.92 (t, J = 7.4 Hz, 3H), 0.81 (d, J = 6.7 Hz, 4H).

MS (ESI +) m / z 413 (M + H) ⁺

Example  584: N- (4- (4-((1,1- Dioxidothiomorpholino ) methyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((1,1-dioxidothiomorpholino) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (s, 1H), 8.03 (s, 1H), 7.70 (d, J = 7.9 Hz, 2H), 7.51 (d, J = 7.9 Hz, 2H), 7.40 (t, J = 3.0 Hz, 1H), 6.63-6.39 (m, 1H), 3.75 (s, 2H), 3.13 (t, J = 5.1 Hz, 5H), 3.01- 2.82 (m, 4H), 2.05 (t, J = 11.7 Hz, 1H), 0.81 (dt, J = 5.7, 10.4 Hz, 4H).

MS (ESI +) m / z 425 (M + H) ⁺

Example  585: N- (4- (4- (4- Oxopiperidine -1 day) methyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4- oxopiperidin -1-yl) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (s, 1H), 8.04 (s, 1H), 7.78-7.66 (m, 2H), 7.53 (d, J = 7.9 Hz, 2H), 7.40 (t, J = 3.0 Hz, 1H), 6.55 (dd, J = 1.8, 3.5 Hz, 1H), 3.70 (s, 2H), 2.74 (t, J = 6.0 Hz, 4H), 2.38 (t, J = 6.0 Hz, 4H), 2.04 (d, J = 8.8 Hz, 1H), 0.91-0.75 (m, 4H).

MS (ESI +) m / z 389 (M + H) ⁺

Example  586: N- (4- (4-((3- Cyanoazetidine -1 day) methyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((3- cyanoazetidin -1-yl) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.61 (s, 1H), 8.02 (s, 1H), 7.75-7.64 (m, 2H), 7.48-7.41 (m, 2H ), 7.40 (dd, J = 2.4, 3.5 Hz, 1H), 6.53 (dd, J = 1.8, 3.5 Hz, 1H), 3.66 (s, 2H), 3.55-3.45 (m, 4H), 2.04 (d, J = 7.0 Hz, 1H), 0.81 (ddd, J = 2.6, 6.4, 11.7 Hz, 4H).

MS (ESI < + >) m / z 372 (M + H) ⁺

Example  587: N- (4- (4-((4- ( Methylsulfonyl Piperazin-1-yl) methyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4- (methylsulfonyl) piperazin-1-yl) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

MS (ESI +) m / z 454 (M + H) ⁺

Example  588: N- (4- (4-((1,1- Dioxidothiomorpholino ) methyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) -2-methylcyclopropane-1-carboxamide (N- (4- (4-((1,1-dioxidothiomorpholino) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin -6-yl) -2-methylcyclopropane-1-carboxamide)

MS (ESI +) m / z 439 (M + H) ⁺

Example  589: N- (4- (4- (1- (1,1- Dioxidothiomorpholino ) Ethyl) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (1- (1,1-dioxidothiomorpholino) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.53 (s, 1H), 10.62 (s, 1H), 8.03 (s, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.54 (d, J = 7.9 Hz, 2H), 7.45-7.36 (m, 1H), 6.55 (s, 1H), 3.99 (s, 1H), 3.10 (s, 4H), 2.93 (s, 4H), 2.05 (s, 1H ), 1.40 (d, J = 6.7 Hz, 3H), 0.83-0.77 (m, 4H).

MS (ESI +) m / z 439 (M + H) ⁺

Example  590: N- (4- (3,5- Difluoro -4-( Morpholinomethyl ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (3,5-difluoro-4- (morpholinomethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.68 (s, 1H), 10.72 (s, 1H), 8.05 (s, 1H), 7.47 (d, J = 2.8 Hz, 1H), 7.44-7.35 ( m, 2H), 6.63-6.55 (m, 1H), 3.63 (s, 2H), 3.56 (t, J = 4.5 Hz, 4H), 2.45-2.42 (m, 2H), 2.04 (s, 1H), 0.86 0.78 (m, 4 H).

MS (ESI +) m / z 413 (M + H) ⁺

Example  591: N- (4- (4- (2- (1,1- Dioxidothiomorpholino ) Ethyl) phenyl) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  Synthesis of (N- (4- (4- (2- (1,1-dioxidothiomorpholino) ethyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.51 (s, 1H), 10.60 (s, 1H), 8.01 (s, 1H), 7.71-7.59 (m, 2H), 7.50-7.34 (m, 3H ), 6.52 (dd, J = 3.5, 1.7 Hz, 1H), 3.10 (d, J = 5.6 Hz, 4H), 3.05-2.93 (m, 4H), 2.86-2.73 (m, 4H), 2.03 (m, 1H), 0.90-0.74 (m, 4H).

MS (ESI +) m / z 439 (M + H) ⁺

Example  592: N- (6- (4-((1,1- Dioxidothiomorpholino ) methyl ) Phenyl) -9H- Purin Synthesis of-2-yl) cyclopropanecarboxamide (N- (6- (4-((1,1-dioxidothiomorpholino) methyl) phenyl) -9H-purin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.79 (s, 1H), 8.88-8.79 (m, 2H), 8.51 (s, 1H), 7.69-7.58 (m, 2H), 3.62-3.55 (m , 2H), 3.29 (d, J = 21.0 Hz, 8H), 2.18 (dd, J = 8.6, 3.7 Hz, 1H), 0.84 (ddt, J = 10.7, 4.9, 2.9 Hz, 4H).

MS (ESI +) m / z 427 (M + H) ⁺

Example  593: N- (7- (4-((5- methyl -2H- Tetrazole -2 days) methyl ) Phenyl) -3H- Imidazo [4,5-b] pyridine -5-yl) cyclopropanecarboxamide (N- (7- (4-((5-methyl-2H-tetrazol-2-yl) methyl) phenyl) -3H-imidazo [4,5-b] pyridin- Synthesis of 5-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 375 (M + H) ⁺

Example  594: N- (7- (4-((5- methyl -1H- Tetrazole -1 day) methyl ) Phenyl) -3H- Imidazo [4,5-b] pyridine -5-yl) cyclopropanecarboxamide (N- (7- (4-((5-methyl-1H-tetrazol-1-yl) methyl) phenyl) -3H-imidazo [4,5-b] pyridin- Synthesis of 5-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 375 (M + H) ⁺

Example  595: N- (4- (4-(((1,1- Dioxydotetrahydrothiophene -3-yl) amino) methyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1,1-dioxidotetrahydrothiophen-3-yl) amino) Synthesis of methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (s, 1H), 8.02 (s, 1H), 7.74-7.65 (m, 2H), 7.51 (d, J = 7.9 Hz, 2H), 7.45-7.38 (m, 1H), 6.58-6.46 (m, 1H), 3.80 (s, 2H), 3.48 (s, 1H), 3.28-3.19 (m, 1H), 3.05 (dt, J = 7.6, 12.6 Hz, 1H), 2.94 (dd, J = 6.5, 13.1 Hz, 1H), 2.70 (d, J = 23.9 Hz, 2H), 2.30-2.23 (m, 1H), 2.04 (dd, J = 7.2, 13.5 Hz, 2H), 0.88-0.78 (m, 4H)

MS (ESI +) m / z 425 (M + H) ⁺

Example  596: N- (4- (4-(((1,1- Dioxydotetrahydro -2H- Thiopyran -4-yl) amino) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1,1- Synthesis of dioxidotetrahydro-2H-thiopyran-4-yl) amino) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.52 (s, 1H), 10.61 (s, 1H), 8.02 (s, 1H), 7.76-7.35 (m, 9H), 6.65-6.47 (m, 1H ), 3.78 (s, 1 H), 3.09 (d, J = 53.8 Hz, 4H), 2.01 (d, J = 52.3 Hz, 5H), 0.89-0.75 (m, 4H).

MS (ESI +) m / z 439 (M + H) ⁺

Example  597: N- (6- (4-(((4- Fluorophenyl Amino) methyl ) Phenyl) -9H- Purin -2 days) Cyclopropanecarboxamide  (N- (6- (4-(((4- fluorophenyl ) amino ) methyl ) phenyl ) -9H-purin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.67 (s, 1H), 8.76 (d, J = 7.9 Hz, 2H), 8.42 (s, 1H), 7.55 (d, J = 8.1 Hz, 2H) , 6.89 (t, J = 8.7 Hz, 2H), 6.58 (dd, J = 8.8, 4.5 Hz, 2H), 6.24 (t, J = 6.1 Hz, 1H), 4.33 (d, J = 6.1 Hz, 2H) , 2.20 (s, 1 H), 0.91-0.79 (m, 4 H).

MS (ESI +) m / z 403 (M + H) ⁺

Example  598: N- (6- (4-(((3- Fluorophenyl Amino) methyl ) Phenyl) -9H- Purin -2 days) Cyclopropanecarboxamide  (N- (6- (4-(((3- fluorophenyl ) amino ) methyl ) phenyl ) -9H-purin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.73 (s, 1H), 8.72 (d, J = 37.7 Hz, 2H), 8.46 (s, 1H), 7.56 (d, J = 8.0 Hz, 2H) , 7.05 (q, J = 7.8 Hz, 2H), 6.65 (q, J = 9.8, 8.1 Hz, 1H), 6.44 (d, J = 8.5 Hz, 1H), 6.41-6.26 (m, 2H), 4.37 ( d, J = 6.1 Hz, 2H), 2.19 (s, 1H), 0.86-0.69 (m, 4H).

MS (ESI +) m / z 403 (M + H) ⁺

Example  599: N- (4- (1- (1-(( Trifluoromethyl Sulfonyl) Azetidine -3-yl) -1H- Pyrazole 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1-((trifluoromethyl) sulfonyl) azetidin-3- yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

Step 1) tert-Butyl 3- (4- (6- (cyclopropanecarboxamido) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-4-yl) -1H-pyrazole-1 Synthesis of -yl) azetidine-1-carboxylate

2.5 g (6.44 mmol) of synthesized N- (4-chloro-1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide was added with DMF / H ₂ O = 2: Dissolve in 1 solution (50 mL), 4 tert-butyl 3- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyra Zol-1-yl) azetidine-1-carboxylate 2.5 g (7.1 mmol), Pd (dppf) Cl ₂ 0.8 g (0.97 mmol) and 1.6 g (7.7 mmol) of K ₃ PO ₄ were added thereto, followed by stirring at 80 ^° C. to 90 ^° C. for 2 hours. When the reaction was completed, the mixture was cooled at room temperature, and after adding water and diluted hydrochloric acid, extracted with ethyl acetate at pH 4-5. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was separated by silica gel column chromatography (n-hexane / ethyl acetate = 1: 1) to obtain tert-butyl 3- (4- (6- (cyclopropane carboxamido) -1-tosyl-1H-pyrrolo [ A mixture containing 2,3-b] pyridin-4-yl) -1H-pyrazol-1-yl) azetidine-1-carboxylate as a main product was obtained.

MS (ESI +) m / z 577 (M + H) ⁺

Step 2) N- (4- (1- (azetidin-3-yl) -1H-pyrazol-4-yl) -1-tosylyl-1H-pyrrolo [2,3-b] pyridine-6- I) Synthesis of cyclopropanecarboxamide

The compound tert-butyl 3- (4- (6- (cyclopropane carboxamido) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-4-yl) -1H-pyrazole-1- I) 5 g of azetidine-1-carboxylate was dissolved in dichloromethane (50 mL), TFA (5 mL) was added thereto, and the mixture was stirred at room temperature for 2 hours. The compound proceeded to the next step without a separate separation process.

MS (ESI +) m / z 477 (M + H) ⁺

Step 3) N- (1-Tosyl-4- (1- (1-((trifluoromethyl) sulfonyl) azetidin-3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo Synthesis of [2,3-b] -cyclopropanecarboxamide

Synthesized N- (4- (1- (azetidin-3-yl) -1H-pyrazol-4-yl) -1-tosylyl-1H-pyrrolo [2,3-b] pyridin-6-yl Cyclopropanecarboxamide (2 g) was dissolved in dichloromethane (20 mL), and Et ₃ N (2 equivalents, 1.17 mL) was added thereto and stirred. Trifluoro methanesulfonylchloride (1.5 equiv, 1.06 g) was added at 0 ^° C., followed by stirring at room temperature for 2 hours to give compound N- (1-tosyl-4- (1- (1-((trifluoromethyl ) Sulfonyl) azetidin-3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b] cyclopropanecarboxamide 1.6 g (41%, 3-step cumulative yield) Obtained.

MS (ESI +) m / z 609 (M + H) ⁺

Step 4) N- (4- (1- (1- (1-trifluoromethyl) sulfonyl) azetidin-3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2, 3-b] Pyridin-6-yl) cyclopropanecarboxamide

Synthesized N- (1-tosyl-4- (1- (1-((trifluoromethyl) sulfonyl) azetidin-3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [ 2,3-b] -cyclopropanecarboxamide was dissolved in 50 mL of MeOH / THF (2: 1) and 10 mL of 2N aqueous sodium hydroxide solution was added and stirred at 30-40 ^° C. for 4 hours. Upon completion, the mixture was cooled at room temperature and extracted with dichloromethane at pH neutral by addition of dilute aqueous hydrochloric acid The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. Target compound Example 599, N- (4- (1- (1- (1-trifluoromethyl) sulfonyl) azetidin-3-yl)-via TLC (DCM: MeOH = 30: 1) method 1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide was obtained.

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.53 (s, 1H), 8.55 (d, J = 9.1 Hz, 1H), 8.20 (s, 1H), 8.07 (s, 1H), 7.47-7.35 (m, 1H), 6.82-6.70 (m, 1H), 5.68-5.55 (m, 1H), 4.71 (dt, J = 7.2, 15.1 Hz, 4H), 2.06 (d, J = 18.0 Hz, 1H), 0.88-0.76 (m, 4H).

MS (ESI +) m / z 455 (M + H) ⁺

Examples 600-611

Hereinafter, in Examples 600 to 611, the synthesis was carried out in the same manner as in Example 599, or by using a suitable reactant in consideration of the reaction scheme 1 and the structure of the compound to be prepared.

Example  600: N- (4- (1- ( Azetidine -3-yl) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- ( azetidin -3- yl ) -1H- pyrazol -4- yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.51 (s, 1H), 8.48 (s, 1H), 8.06 (s, 2H), 7.37 (s, 1H), 6.73 ( s, 1H), 5.32 (s, 1H), 4.04 (s, 2H), 3.83 (d, J = 10.2 Hz, 2H), 2.00 (s, 3H), 1.47 (s, 2H), 0.84 (s, 4H ).

MS (ESI +) m / z 323 (M + H) ⁺

Example  601: N- (4- (1- (1- ( Ethylsulfonyl ) Azetidine -3-yl) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (ethylsulfonyl) azetidin-3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b ] synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.52 (s, 1H), 8.50 (s, 1H), 8.14 (s, 1H), 8.06 (s, 1H), 7.38 ( s, 1H), 6.73 (d, J = 3.5 Hz, 1H), 5.41 (p, J = 7.1 Hz, 1H), 4.39 (dd, J = 6.4, 8.6 Hz, 2H), 4.28 (t, J = 8.2 Hz, 2H), 3.25 (q, J = 7.4 Hz, 2H), 2.07-1.99 (m, 1H), 1.28 (t, J = 7.3 Hz, 3H), 0.81 (dt, J = 3.3, 15.8 Hz, 4H ).

MS (ESI +) m / z 415 (M + H) ⁺

Example  602: N- (4- (1- (1- ( Butylsulfonyl ) Azetidine -3-yl) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (butylsulfonyl) azetidin-3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b ] synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 10.53 (d, J = 6.6 Hz, 1H), 8.50 (s, 1H), 8.10 (d, J = 29.3 Hz, 2H) , 7.38 (s, 1H), 6.80-6.66 (m, 1H), 5.41 (s, 1H), 4.34 (dq, J = 8.8, 9.7, 40.3 Hz, 4H), 3.27-3.19 (m, 2H), 2.04 (s, 1H), 1.71 (d, J = 10.7 Hz, 2H), 1.52-1.39 (m, 2H), 1.03-0.89 (m, 4H), 0.82 (s, 4H).

MS (ESI +) m / z 443 (M + H) ⁺

Example  603: N- (4- (1- (1- ( Methylsulfonyl ) Azetidine -3-yl) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (methylsulfonyl) azetidin-3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b ] synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.53 (s, 1H), 8.52 (s, 1H), 8.10 (d, J = 31.4 Hz, 2H), 7.38 (s, 1H), 6.74 (s, 1H), 5.50-5.31 (m, 1H), 4.33 (dd, J = 8.8, 16.6 Hz, 4H), 3.15 (p, J = 6.0 Hz, 3H), 2.03 (s, 1H ), 0.83 (d, J = 6.3 Hz, 4H).

MS (ESI +) m / z 401 (M + H) ⁺

Example  604: N- (4- (1- (1- ( Phenylsulfonyl ) Azetidine -3-yl) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (phenylsulfonyl) azetidin-3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b ] synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.51 (s, 1H), 8.21 (s, 1H), 8.03-7.86 (m, 4H), 7.76 (q, J = 8.2 , 14.4 Hz, 3H), 7.36 (s, 1H), 6.62 (s, 1H), 5.24 (s, 1H), 4.18 (dt, J = 9.0, 38.6 Hz, 4H), 2.03 (s, 1H), 0.88 0.73 (m, 4 H).

MS (ESI +) m / z 463 (M + H) ⁺

Example  605: N- (4- (1- ( 1, (3,4-difluorophenyl) sulfonyl ) Azetidine -3-yl) -1H- Pyrazole 4-yl) -1H-pyrrolo [2,3-b] pyridine-6-cyclopropanecarboxamide (N- (4- (1- (1-((3,4-difluorophenyl) sulfonyl) azetidin- Synthesis of 3-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.51 (s, 1H), 8.31 (s, 1H), 7.98 (d, J = 21.8 Hz, 2H), 7.75 (d, J = 12.9 Hz, 2H), 7.48 (s, 1H), 7.36 (s, 1H), 6.64 (s, 1H), 5.23 (s, 1H), 4.19 (d, J = 24.7 Hz, 4H), 3.96 ( s, 3H), 2.02 (s, 1H), 0.80 (d, J = 15.3 Hz, 4H).

MS (ESI +) m / z 499 (M + H) ⁺

Example  606: N- (4- (1- (1- ( Cyclohexylsulfonyl ) Azetidine -3-yl) -1H- Pyrazole 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (1- (cyclohexylsulfonyl) azetidin-3-yl)- 1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.52 (s, 1H), 8.49 (s, 1H), 8.11 (d, J = 31.0 Hz, 2H), 7.44-7.30 ( m, 1H), 6.73 (s, 1H), 5.40 (d, J = 9.8 Hz, 1H), 4.44-4.15 (m, 4H), 3.11 (s, 1H), 2.08 (d, J = 12.9 Hz, 3H ), 1.80 (d, J = 11.5 Hz, 2H), 1.64 (s, 1H), 1.27 (dd, J = 35.0, 51.6 Hz, 7H), 0.81 (d, J = 16.2 Hz, 4H).

MS (ESI +) m / z 469 (M + H) ⁺

Example  607: N- (4- (1- (1- ( Methylsulfonyl ) Piperidin-4-yl) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (methylsulfonyl) piperidin-4-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b ] synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (s, 1H), 10.50 (s, 1H), 8.43 (s, 1H), 8.02 (d, J = 16.4 Hz, 2H), 7.36 (s, 1H), 6.75 (s, 1H), 4.44 (s, 1H), 3.70 (d, J = 11.9 Hz, 2H), 2.95 (d, J = 6.9 Hz, 5H), 2.27-1.98 (m, 6H), 0.86-0.75 (m, 4H).

MS (ESI +) m / z 429 (M + H) ⁺

Example  608: N- (4- (1- (1- ( Ethylsulfonyl ) Piperidin-4-yl) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (ethylsulfonyl) piperidin-4-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b ] synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (s, 1H), 10.49 (s, 1H), 8.42 (s, 1H), 8.02 (d, J = 16.8 Hz, 2H), 7.42-7.32 ( m, 1H), 6.75 (d, J = 3.2 Hz, 1H), 4.44 (d, J = 12.9 Hz, 1H), 3.74 (d, J = 12.2 Hz, 2H), 3.07 (ddd, J = 8.6, 13.4 , 31.8 Hz, 4H), 2.20-1.96 (m, 5H), 1.24 (t, J = 7.3 Hz, 3H), 0.80 (d, J = 17.7 Hz, 4H).

MS (ESI +) m / z 443 (M + H) ⁺

Example  609: N- (4- (1- (1-(( Trifluoromethyl ) Sulfonyl) piperidin-4-yl) -1H- Pyrazole 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1-((trifluoromethyl) sulfonyl) piperidin-4- yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.50 (s, 1H), 8.41 (d, J = 34.0 Hz, 1H), 8.03 (d, J = 12.2 Hz, 2H) , 7.36 (s, 1H), 6.75 (s, 1H), 3.94 (d, J = 13.2 Hz, 2H), 2.90 (d, J = 12.4 Hz, 1H), 2.26-1.99 (m, 6H), 0.86- 0.76 (m, 4 H).

MS (ESI +) m / z 483 (M + H) ⁺

Example  610: N- (4- (1- (1- (2- Cyanoacetyl ) Azetidine -3-yl) -1H- Pyrazole 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (2-cyanoacetyl) azetidin-3-yl ) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.52 (s, 1H), 8.56 (s, 1H), 8.12 (s, 1H), 8.07 (s, 1H), 7.38 ( t, J = 3.0 Hz, 1H), 6.77-6.71 (m, 1H), 5.41 (t, J = 6.7 Hz, 1H), 4.64 (t, J = 8.6 Hz, 1H), 4.56-4.49 (m, 1H ), 4.41 (t, J = 9.3 Hz, 1H), 4.28 (dd, J = 10.2, 5.4 Hz, 1H), 3.84 (d, J = 3.5 Hz, 2H), 2.04-1.96 (m, 1H), 0.84 0.77 (m, 4 H).

MS (ESI +) m / z 390 (M + H) ⁺

Example  611: N- (4- (1- (1- ( Cyanomethyl ) Piperidin-4-yl) -1H- Pyrazole -4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (cyanomethyl) piperidin-4-yl) -1H-pyrazol-4-yl) -1H-pyrrolo [2,3-b ] synthesis of pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.39 (s, 1H), 10.49 (s, 1H), 8.39 (s, 1H), 8.01 (d, J = 19.9 Hz, 3H), 7.39-7.30 ( m, 1H), 6.73 (s, 1H), 4.44-4.18 (m, 2H), 2.93 (d, J = 11.1 Hz, 4H), 2.37 (s, 3H), 2.09 (d, J = 8.3 Hz, 7H ), 0.80 (d, J = 18.3 Hz, 7H).

MS (ESI +) m / z 390 (M + H) ⁺

Example  612: N- (4- (1- (3- ( Cyanomethyl ) Oxetane -3-yl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) oxetan-3-yl) -1,2,3, Synthesis of 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

1.0 g of the above synthesized N- (4- (1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane carboxamide (3.5 mmol) was dissolved in acetonitrile, 0.4 g (3.9 mmol) of 2- (oxetane-3-ylidene) acetonitrile, 1.6 g (10.5 mmol) of DBU were added, and the mixture was stirred at 30-40 ^o C for 16 hours. Stirred. When the reaction was completed, the mixture was cooled to room temperature, water was added, and then extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was separated by silica gel column chromatography (DCM / MeOH = 30: 1) to give N- (4- (1- (3- (cyanomethyl) oxetan-3-yl) -1,2,3, 6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] cyclopropanecarboxamide was obtained.

MS (ESI +) m / z 378 (M + H) ⁺

Examples 613-628

Hereinafter, in Examples 613 to 628, synthesis was carried out in the same manner as in Example 612, or by using a suitable reactant in consideration of Scheme 1 and the structure of the compound to be prepared.

Example  613: N- (4- (1- (3- ( Cyanomethyl ) Oxetane -3-yl) -3- methyl -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) oxetan-3-yl) -3- Synthesis of methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.40 (s, 1H), 10.54 (s, 1H), 7.81 (s, 1H), 7.35-7.26 (m, 1H), 6.46 (d, J = 3.8 Hz, 1H), 6.09 (s, 1H), 4.64 (d, J = 6.6 Hz, 1H), 4.53 (d, J = 6.6 Hz, 1H), 4.43 (t, J = 7.0 Hz, 2H), 3.27 ( d, J = 18.0 Hz, 1H), 3.15 (d, J = 17.0 Hz, 1H), 3.08 (d, J = 3.8 Hz, 2H), 2.96 (s, 1H), 2.76-2.65 (m, 2H), 2.40 (dd, J = 4.6, 11.2 Hz, 1H), 2.02 (s, 1H), 0.91 (d, J = 6.9 Hz, 3H), 0.81-0.76 (m, 4H).

MS (ESI +) m / z 392 (M + H) ⁺

Example  614: tert-butyl3- (cyanomethyl) -3- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6 -Dihydropyridin-1 (2H) -yl) azetidine-1-carboxylate ( tert - butyl  3- (cyanomethyl) -3- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6-dihydropyridin-1 (2H) -yl) azetidine- 1-carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.53 (s, 1H), 7.85 (s, 1H), 7.33 (t, J = 3.0 Hz, 1H), 6.53 (dd, J = 3.6, 1.8 Hz, 1H), 6.31 (d, J = 3.9 Hz, 1H), 3.83 (d, J = 35.4 Hz, 4H), 3.29-3.21 (m, 2H), 3.03 (s, 2H), 2.72-2.62 (m, 2H), 2.55 (s, 2H), 2.08-1.96 (m, 1H), 1.39 (s, 9H), 0.82-0.75 (m, 4H).

MS (ESI +) m / z 477 (M + H) ⁺

Example  615: N- (4- (1- (3- ( Cyanomethyl ) Azetidine -3-yl) -1,2,3,6- Tetrahydropyridine -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropane Carboxamide  (N- (4- (1- (3- (cyanomethyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6 -yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 10.55 (s, 1H), 7.86 (s, 1H), 7.34 (t, J = 3.1 Hz, 1H), 6.53 (d, J = 2.6 Hz, 1H), 6.35 (s, 1H), 3.89 (d, J = 10.4 Hz, 2H), 3.76 (d, J = 10.4 Hz, 2H), 3.09 (s, 2H), 2.75 (t, J = 5.4 Hz, 2H), 2.58 (s, 2H), 2.02 (s, 1H), 0.87-0.73 (m, 4H).

MS (ESI +) m / z 377 (M + H) ⁺

Example  616: N- (4- (1- (3- (cyanomethyl) -1- (ethylsulfonyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) -1- (ethylsulfonyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.53 (s, 1H), 7.86 (s, 1H), 7.33 (t, J = 3.0 Hz, 1H), 6.54 (t, J = 2.7 Hz, 1H), 6.33 (d, J = 3.4 Hz, 1H), 4.00 (d, J = 8.2 Hz, 2H), 3.75 (d, J = 8.2 Hz, 2H), 3.28 (d, J = 3.3 Hz, 2H), 3.17 (q, J = 7.3 Hz, 2H), 3.11 (s, 2H), 2.70 (t, J = 5.4 Hz, 2H), 2.55 (s, 2H), 2.06-1.96 (m, 1H), 1.25 (t, J = 7.3 Hz, 3H), 0.82-0.75 (m, 4H).

MS (ESI +) m / z 469 (M + H) ⁺

Example  617: N- (4- (1- (3- (cyanomethyl) -1- (isopropylsulfonyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) -1- (isopropylsulfonyl) azetidin-3-yl ) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.53 (s, 1H), 7.85 (s, 1H), 7.36-7.29 (m, 1H), 6.54 (dd, J = 3.5 , 1.9 Hz, 1H), 6.32 (s, 1H), 4.01 (d, J = 7.9 Hz, 2H), 3.72 (d, J = 7.9 Hz, 2H), 3.24 (s, 2H), 3.10 (s, 2H ), 2.67 (d, J = 6.0 Hz, 2H), 2.02 (s, 1H), 1.26 (d, J = 6.8 Hz, 6H), 1.17 (s, 1H), 0.80 (q, J = 3.4 Hz, 4H ).

MS (ESI +) m / z 483 (M + H) ⁺

Example  618: N- (4- (1- (3- (cyanomethyl) -1-((3-cyanopropyl) sulfonyl) azetidin-3-yl) -1,2,3,6-tetrahydro Pyridin-4-yl) -1H-pyrrolo [[2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) -1-(( Synthesis of 3-cyanopropyl) sulfonyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.53 (s, 1H), 7.86 (s, 1H), 7.34 (t, J = 2.9 Hz, 1H), 6.54 (dt, J = 5.0, 2.5 Hz, 1H), 6.32 (s, 1H), 4.00 (s, 1H), 3.78 (d, J = 8.2 Hz, 1H), 3.29 (d, J = 6.3 Hz, 2H), 3.14 ( d, J = 12.4 Hz, 2H), 2.71 (d, J = 7.1 Hz, 2H), 2.66 (t, J = 7.3 Hz, 2H), 2.56 (s, 2H), 2.02 (d, J = 7.5 Hz, 2H), 0.82-0.74 (m, 4H).

MS (ESI +) m / z 508 (M + H) ⁺

Example  619: N- (4- (1- (3- ( Cyclomethyl Sulfonyl) Azetidine -3-yl) -1,2,3,6- Tetrahydropyridine 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) -1-((trifluoromethyl) synthesis of sulfonyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.43 (s, 1H), 10.54 (s, 1H), 7.86 (s, 1H), 7.34 (t, J = 3.0 Hz, 1H), 6.54 (dd, J = 3.6, 1.9 Hz, 1H), 6.32 (d, J = 3.8 Hz, 1H), 4.35-4.18 (m, 4H), 3.29 (d, J = 3.4 Hz, 2H), 3.15 (s, 2H), 2.71 (t, J = 5.5 Hz, 2H), 2.57 (s, 2H), 2.01 (d, J = 7.5 Hz, 1H), 0.83-0.77 (m, 4H).

MS (ESI +) m / z 509 (M + H) ⁺

Example  620: N- (4- (1- (3- (cyanomethyl) -1- (piperidin-4-yl) azetidin-3-yl) -1,2,3,6-tetrahydropyridine- 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) -1- (piperidin-4- yl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.57 (s, 1H), 11.00 (s, 1H), 9.45 (s, 1H), 8.77 (s, 1H), 7.80 (s, 1H), 7.39 ( s, 1H), 6.59 (s, 1H), 6.39 (s, 1H), 4.15 (d, J = 10.7 Hz, 2H), 3.70-3.58 (m, 2H), 3.56 (s, 1H), 3.54-3.46 (m, 2H), 3.46-3.33 (m, 2H), 2.97 (s, 2H), 2.84 (dd, J = 22.8, 10.4 Hz, 2H), 2.67 (s, 2H), 2.18-1.93 (m, 3H ), 1.88-1.68 (m, 2H), 0.83 (m, 4H).

MS (ESI +) m / z 460 (M + H) ⁺

Example  621: N- (4- (1- (3- (cyanomethyl) -1- (1- (4- (trifluoromethyl) thiazole-2-carbonyl) piperidin-4-yl) ase Thidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- ( 4- (1- (3- (cyanomethyl) -1- (1- (4- (trifluoromethyl) thiazole-2-carbonyl) piperidin-4-yl) azetidin-3-yl) -1,2,3,6- tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.52 (s, 1H), 8.77 (s, 1H), 7.85 (s, 1H), 7.38-7.30 (m, 1H), 6.53 (s, 1H), 6.33 (s, 1H), 4.47-4.44 (m, 1H), 3.98-3.97 (m, 1H), 3.83-3.78 (m, 1H), 3.31-3.21 (m, 4H), 3.15-3.02 (m, 4H), 2.72 (m, 2H), 2.03-1.96 (m, 1H), 1.78-1.69 (m, 2H), 1.38-1.26 (m, 2H) 0.79 (dd, J = 9.4, 6.2 Hz, 4H).

MS (ESI +) m / z 639 (M + H) ⁺

Example  622: N- (4- (1- (1- (1- (2- ( Cyanoacetyl ) Piperidin-4-yl) -3- ( Cyanomethyl ) Azetidin-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (1- (1- (1- (2-cyanoacetyl) ) piperidin-4-yl) -3- (cyanomethyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (s, 1H), 10.53 (s, 1H), 7.84 (s, 1H), 7.33 (d, J = 3.3 Hz, 1H), 6.53 (s, 1H), 6.32 (s, 1H), 4.02 (s, 2H), 3.90-3.18 (m, 1H), 3.52 (m, 1H), 3.30-3.18 (m, 4H), 3.16-2.93 (m, 5H) , 2.80-2.63 (m, 2H), 2.43-2.25 (m, 2H), 2.07-1.93 (m, 1H), 1.71-1.53 (m, 2H), 1.19-1.05 (m, 2H), 0.85-0.77 ( m, 4H).

MS (ESI +) m / z 527 (M + H) ⁺

Example  623: N- (4- (1- (3- (cyanomethyl) -1-((4-fluorophenyl) sulfonyl) azetidin-3-yl) -1,2,3,6-tetrahydro Pyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) -1-((4 -fluorophenyl) sulfonyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.52 (s, 1H), 7.98-7.91 (m, 2H), 7.81 (s, 1H), 7.50-7.42 (m, 2H ), 7.33 (dd, J = 3.5, 2.4 Hz, 1H), 6.48 (dd, J = 3.5, 1.9 Hz, 1H), 6.18 (d, J = 3.2 Hz, 1H), 3.76 (s, 4H), 3.07 (d, J = 3.5 Hz, 2H), 2.96 (s, 2H), 2.33 (s, 2H), 2.01 (d, J = 4.9 Hz, 1H), 0.79 (dt, J = 11.0, 3.5 Hz, 4H) .

MS (ESI +) m / z 535 (M + H) ⁺

Example  624: 3- (cyanomethyl) -3- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6-dihydro Pyridin-1 (2H) -yl) -N- (2,2,2-trifluoroethyl) azetidine-1-carboxamide (3- (cyanomethyl) -3- (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,6-dihydropyridin-1 (2H) -yl) -N- (2,2,2-trifluoroethyl) azetidine-1-carboxamide) synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.42 (d, J = 2.6 Hz, 1H), 10.53 (s, 1H), 7.85 (s, 1H), 7.33 (dd, J = 3.5, 2.5 Hz, 1H), 6.53 (dd, J = 3.6, 1.9 Hz, 1H), 6.34 (d, J = 3.3 Hz, 1H), 4.25 (d, J = 9.2 Hz, 1H), 4.12 (d, J = 9.1 Hz, 1H), 3.93 (d, J = 10.3 Hz, 1H), 3.83 (d, J = 10.2 Hz, 1H), 3.41 (dd, J = 11.3, 3.4 Hz, 2H), 3.10 (s, 2H), 2.75- 2.66 (m, 2H), 2.55 (d, J = 7.1 Hz, 2H), 2.01 (q, J = 8.5, 6.4 Hz, 1H), 0.79 (ddd, J = 11.3, 6.3, 2.6 Hz, 4H).

MS (ESI +) m / z 502 (M + H) ⁺

Example  625: N- (4- (1- (3- (cyanomethyl) -1- (3,3,3-trifluoropropanoyl) azetidin-3-yl) -1,2,3,6 -Tetrahydropyridin-4-yl) pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) -1- (3, Synthesis of 3,3-trifluoropropanoyl) azetidin-3-yl) -1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44-11.35 (m, 1H), 10.53 (s, 1H), 7.85 (s, 1H), 7.36-7.27 (m, 1H), 7.17 (t, J = 6.3 Hz, 1H), 6.55 (dd, J = 3.9, 2.1 Hz, 1H), 6.33 (d, J = 3.6 Hz, 1H), 3.88 (d, J = 8.7 Hz, 2H), 3.83-3.72 (m , 4H), 3.08 (s, 2H), 2.69 (d, J = 5.7 Hz, 2H), 2.56 (s, 2H), 2.02-1.97 (m, 1H), 0.81-0.75 (m, 4H).

MS (ESI +) m / z 487 (M + H) ⁺

Example  626: N- (4- (1- (3- (cyanomethyl) -1- (ethylsulfonyl) azetidin-3-yl) -3-methyl-1,2,3,6-tetrahydropyridine- 4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (1- (3- (cyanomethyl) -1- (ethylsulfonyl) azetidin- Synthesis of 3-yl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Chloroform-d) δ 11.40 (s, 1H), 10.54 (s, 1H), 7.80 (s, 1H), 7.36-7.25 (m, 1H), 6.45 (dd, J = 1.9, 3.5 Hz, 1H), 6.07 (s, 1H), 4.01 (dd, J = 8.3, 13.4 Hz, 1H), 3.90 (d, J = 8.3 Hz, 1H), 3.73 (dd, J = 8.1, 11.7 Hz, 2H), 3.23-3.07 (m, 4H), 2.95 (s, 1H), 2.77-2.65 (m, 1H), 2.07 (s, 3H), 1.99 (d, J = 6.5 Hz, 1H), 1.25-1.21 (m, 3 H), 0.82-0.73 (m, 4 H).

MS (ESI +) m / z 483 (M + H) ⁺

Example  627: (S) -N- (4- (1- (3- (cyanomethyl) -1- (ethylsulfonyl) azetidin-3-yl) -3-methyl-1,2,3,6- Tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- (3- (cyanomethyl)) -1- (ethylsulfonyl) azetidin-3-yl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide) Synthesis of

MS (ESI +) m / z 483 (M + H) ⁺

Example  628: (S) -N- (4- (1- (3- (cyanomethyl) -1-((trifluoromethyl) sulfonyl) azetidin-3-yl) -3-methyl-1,2 , 3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (1- ( 3- (cyanomethyl) -1-((trifluoromethyl) sulfonyl) azetidin-3-yl) -3-methyl-1,2,3,6-tetrahydropyridin-4-yl) -1H-pyrrolo [2,3-b] Synthesis of pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 523 (M + H) ⁺

Examples 629-644

Hereinafter, in Examples 629 to 644, the synthesis was carried out in the same manner as in Example 1, or by using the appropriate reactants in consideration of the reaction scheme 1 and the structure of the compound to be prepared.

Example 629: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenylethanesulfonate (4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3- b] pyridin-4-yl) phenyl ethanesulfonate ) Synthesis

MS (ESI +) m / z 386 (M + H) ⁺

Example 630: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl4-fluorobenzenesulfonate (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl 4- fluorobenzenesulfonate ) Synthesis

MS (ESI +) m / z 452 (M + H) ⁺

Example 631: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl propane-1- Sulfonate  (4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3- b] pyridin-4-yl) phenyl propane -One- sulfonate ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.66 (s, 1H), 8.05 (s, 1H), 7.82 (d, J = 8.1 Hz, 2H), 7.50 (d, J = 8.1 Hz, 2H), 7.44 (s, 1H), 6.55 (s, 1H), 3.58 (t, J = 7.6 Hz, 2H), 2.05 (s, 1H), 1.89 (q, J = 8.0, 7.6 Hz, 2H), 1.06 (t, J = 7.5 Hz, 3H), 0.89-0.74 (m, 4H).

MS (ESI +) m / z 400 (M + H) ⁺

Example 632: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl butane-1- Sulfonate  (4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3- b] pyridin-4-yl) phenyl butane -One- sulfonate ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.66 (s, 1H), 8.04 (s, 1H), 7.91-7.74 (m, 2H), 7.50 (d, J = 8.3 Hz, 2H), 7.44 (t, J = 3.2 Hz, 1H), 6.54 (s, 1H), 3.67-3.53 (m, 2H), 2.05 (s, 1H), 1.84 (s, 2H), 1.48 (q , J = 7.6 Hz, 2H), 0.93 (t, J = 7.3 Hz, 3H), 0.86-0.72 (m, 4H).

MS (ESI +) m / z 414 (M + H) ⁺

Example 633: 4 -(6- ( Cyclopropanecarboxamido 1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl propane-2- Sulfonate  (4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3- b] pyridin-4-yl) phenyl propane -2- sulfonate ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.66 (s, 1H), 8.04 (s, 1H), 7.82 (d, J = 8.1 Hz, 2H), 7.49 (d, J = 8.1 Hz, 2H), 7.44 (s, 1H), 6.60-6.50 (m, 1H), 3.87-3.73 (m, 1H), 2.05 (s, 1H), 1.47 (d, J = 6.5 Hz, 6H ), 0.89-0.72 (m, 4H).

MS (ESI +) m / z 400 (M + H) ⁺

Example 634: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl Cyclohexanesulfonate  (4- (6- ( cyclopropanecarboxamido ) -1H- pyrrolo [2,3- b] pyridin-4-yl) phenyl cyclohexanesulfonate ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.66 (s, 1H), 8.04 (s, 1H), 7.81 (d, J = 8.3 Hz, 2H), 7.48 (d, J = 8.3 Hz, 2H), 7.44 (s, 1H), 6.54 (s, 1H), 3.61 (s, 1H), 2.24 (d, J = 12.1 Hz, 2H), 2.05 (s, 1H), 1.84 ( d, J = 12.8 Hz, 2H), 1.70-1.53 (m, 3H), 1.40 (d, J = 13.4 Hz, 2H), 1.24 (t, J = 12.9 Hz, 1H), 0.87-0.74 (m, 4H ).

MS (ESI +) m / z 440 (M + H) ⁺

Example 635: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl3-fluoropropane-1-sulfonate (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl 3- fluoropropane -One- sulfonate ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.66 (s, 1H), 8.05 (s, 1H), 7.86-7.76 (m, 2H), 7.52 (d, J = 8.2 Hz, 2H), 7.44 (d, J = 3.4 Hz, 1H), 6.54 (s, 1H), 4.61 (dt, J = 47.2, 6.0 Hz, 2H), 3.70 (t, J = 7.7 Hz, 2H), 2.27 (d, J = 25.7 Hz, 3H), 2.05 (s, 1H), 0.87-0.75 (m, 4H).

MS (ESI +) m / z 418 (M + H) ⁺

Example 636: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl pro-2-ene-1- Sulfonate  (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl prop -2- ene -One- sulfonate ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.66 (s, 1H), 8.05 (s, 1H), 7.82 (d, J = 8.3 Hz, 2H), 7.57-7.47 ( m, 2H), 7.45-7.38 (m, 1H), 6.60-6.45 (m, 1H), 5.95 (ddt, J = 17.2, 10.3, 6.9 Hz, 1H), 5.58 (dd, J = 31.7, 13.6 Hz, 2H), 4.44 (d, J = 7.2 Hz, 2H), 2.04 (d, J = 8.2 Hz, 1H), 0.82 (dt, J = 10.0, 5.6 Hz, 4H).

MS (ESI +) m / z 398 (M + H) ⁺

Example 637: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl Cyclohexyl methanesulfonate  (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl cyclohexylmethanesulfonate ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.66 (s, 1H), 8.04 (s, 1H), 7.82 (d, J = 8.2 Hz, 2H), 7.50 (d, J = 8.2 Hz, 2H), 7.44 (s, 1H), 6.54 (s, 1H), 3.51 (d, J = 6.5 Hz, 2H), 2.04 (s, 2H), 1.92 (d, J = 12.8 Hz, 2H), 1.69 (d, J = 11.0 Hz, 2H), 1.63 (s, 1H), 1.26 (t, J = 12.6 Hz, 2H), 1.20-1.07 (m, 3H), 0.80 (d, J = 11.1 Hz, 4H).

MS (ESI +) m / z 454 (M + H) ⁺

Example 638: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl (tetrahydrofuran-3-yl) Methanesulfonate  Synthesis of (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl (tetrahydrofuran-3-yl) methanesulfonate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.59 (s, 1H), 10.66 (s, 1H), 8.04 (s, 1H), 7.82 (d, J = 7.9 Hz, 2H), 7.52 (d, J = 8.2 Hz, 2H), 7.44 (s, 1H), 6.54 (s, 1H), 3.92 (t, J = 7.8 Hz, 1H), 3.77 (d, J = 7.1 Hz, 3H), 3.68 (d, J = 8.0 Hz, 1H), 2.17 (s, 1H), 2.05 (s, 1H), 1.76 (d, J = 11.5 Hz, 1H), 1.15-1.03 (m, 1H), 0.82 (s, 4H).

MS (ESI +) m / z 442 (M + H) ⁺

Example 639: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl3-cyanopropane-1-sulfonate (4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl 3- cyanopropane -One- sulfonate ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.66 (s, 1H), 8.05 (s, 1H), 7.83 (d, J = 8.2 Hz, 2H), 7.54 (d, J = 8.3 Hz, 2H), 7.44 (d, J = 3.7 Hz, 1H), 6.54 (s, 1H), 3.69 (t, J = 7.5 Hz, 2H), 2.73 (t, J = 7.3 Hz, 2H) , 2.21 (q, J = 7.7 Hz, 2H), 2.05 (s, 1H), 0.85-0.76 (m, 4H).

MS (ESI +) m / z 425 (M + H) ⁺

Example 640: 4 -(1- (3- Cyanopropyl ) -6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) phenyl3-cyanopropane-1-sulfonate (4- (1- (3- cyanopropyl Synthesis of) -6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) phenyl 3-cyanopropane-1-sulfonate

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.94 (s, 1H), 8.28 (s, 1H), 7.82 (d, J = 8.3 Hz, 2H), 7.69 (d, J = 4.1 Hz, 1H) , 7.57 (d, J = 8.2 Hz, 2H), 6.86 (s, 1H), 4.12 (d, J = 9.1 Hz, 2H), 3.71 (d, J = 8.0 Hz, 2H), 2.72 (d, J = 7.3 Hz, 2H), 2.63 (d, J = 5.1 Hz, 2H), 2.20 (s, 2H), 1.92 (s, 1H), 1.83 (t, J = 7.2 Hz, 2H), 0.85 (d, J = 6.5 Hz, 4H).

MS (ESI +) m / z 492 (M + H) ⁺

Example  641: N- (4- (4-((4- Fluorobenzyl ) Oxy ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((4- fluorobenzyl ) oxy ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 11.49 (s, 1H), 10.58 (s, 1H), 7.99 (s, 1H), 7.75-7.63 (m, 2H), 7.55 (dd, J = 5.6 , 8.4 Hz, 2H), 7.38 (t, J = 2.9 Hz, 1H), 7.29-7.13 (m, 5H), 6.52 (dd, J = 1.7, 3.5 Hz, 1H), 2.13-1.87 (m, 2H) , 0.82 (td, J = 6.2, 12.0, 14.1 Hz, 5H).

MS (ESI +) m / z 402 (M + H) ⁺

Example  642: N- (4- (4- (2- Morpholinoethoxy ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- morpholinoethoxy ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.58 (s, 1H), 7.99 (s, 1H), 7.69-7.61 (m, 2H), 7.38 (dd, J = 2.5 , 3.5 Hz, 1H), 7.17-7.07 (m, 2H), 6.52 (dd, J = 1.9, 3.5 Hz, 1H), 4.17 (t, J = 5.7 Hz, 2H), 3.66-3.53 (m, 4H) , 2.73 (t, J = 5.7 Hz, 2H), 2.09-1.99 (m, 1H), 1.24 (d, J = 3.6 Hz, 3H), 0.85-0.73 (m, 4H).

MS (ESI +) m / z 407 (M + H) ⁺

Example  643: N- (4- (4- Butoxyphenyl ) -1H- Pyrrolo [2,3-b] pyridine -6- days) Cyclopropanecarboxamide  (N- (4- (4- butoxyphenyl ) -1H- pyrrolo [2,3-b] pyridin -6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.48 (s, 1H), 10.57 (s, 1H), 7.99 (s, 1H), 7.70-7.60 (m, 2H), 7.38 (d, J = 3.5 Hz, 1H), 7.13-7.05 (m, 2H), 6.53 (d, J = 3.5 Hz, 1H), 4.05 (t, J = 6.4 Hz, 2H), 2.04 (s, 1H), 1.78-1.67 (m , 2H), 1.47 (h, J = 7.3 Hz, 2H), 0.96 (t, J = 7.4 Hz, 3H), 0.87-0.75 (m, 4H).

MS (ESI +) m / z 350 (M + H) ⁺

Example  644: N- (6- (4-((6- Cyanopyridine -3 days) Methoxy ) Phenyl) -9H- Purin -2 days) Cyclopropanecarboxamide  (N- (6- (4-((6- cyanopyridin -3- yl ) methoxy ) phenyl ) -9H-purin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.73 (s, 1H), 8.90 (d, J = 2.0 Hz, 1H), 8.84 (d, J = 8.8 Hz, 2H), 8.45 (s, 1H) , 8.18 (dd, J = 8.1, 2.1 Hz, 1H), 8.10 (d, J = 7.9 Hz, 1H), 7.27 (d, J = 9.0 Hz, 2H), 5.38 (s, 2H), 2.20-2.13 ( m, 1H), 0.84 (tt, J = 8.0, 3.1 Hz, 4H).

MS (ESI +) m / z 412 (M + H) ⁺

Example  645: N- (4- (4- ( Ethylsulfonamido ) Cyclohexyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( ethylsulfonamido ) cyclohexyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

The synthesized N- (4- (4-aminocyclohex-1-en-1-yl) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide 1 g was dissolved in 20 mL of MeOH, 0.1 g of Pd / C was added and stirred under hydrogen gas for 16 h at room temperature. Upon completion of the reaction, the mixture was celite filtered and washed with MeOH. The filtrate was concentrated to give the product N- (4- (4-aminocyclohexyl) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide.

Example 1 obtained by using N- (4- (4-aminocyclohexyl) -1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide as a starting material In the same manner as in the final product N- (4- (4- (4- (ethylsulfonamido) cyclohexyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide was obtained.

MS (ESI +) m / z 391 (M + H) ⁺

Example  646 to 659

Hereinafter, in Examples 646 to 659, the synthesis was carried out in the same manner as in Example 645, or by using a suitable reactant in consideration of the reaction scheme 1 and the structure of the compound to be prepared.

Example  646: N- (4- (8- ( Ethylsulfonyl )-8- Azabicyclo [3.2.1] octane -3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (8- (ethylsulfonyl) -8-azabicyclo [3.2.1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin- Synthesis of 6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 403 (M + H) ⁺

Example  647: N- (4- (8- ( Cyclopropylsulfonyl )-8- Azabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (cyclopropylsulfonyl) -8-azabicyclo [3.2.1] octan Synthesis of -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 415 (M + H) ⁺

Example  648: N- (4- (8-((3- Fluoropropyl ) Sulfonyl) -8- Azabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8-((3-fluoropropyl) sulfonyl) -8-azabicyclo [ 3.2.1] Synthesis of octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 435 (M + H) ⁺

Example  649: N- (4- (8-((3,4- Difluorophenyl ) Sulfonyl) -8- Azabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8-((3,4-difluorophenyl) sulfonyl) -8- Synthesis of azabicyclo [3.2.1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 487 (M + H) ⁺

Example  650: N- (4- (8- ( Cyclopropanecarbonyl )-8- Azabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (cyclopropanecarbonyl) -8-azabicyclo [3.2.1] octan Synthesis of -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 379 (M + H) ⁺

Example  651: N- (4- (8- Pentanoyl -8- Azabicyclo [3.2.1] octane -3-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (8-pentanoyl-8-azabicyclo [3.2.1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6- yl) cyclopropanecarboxamide)

MS (ESI +) m / z 395 (M + H) ⁺

Example  652: N- (4- (1- (2- Cyanoacetyl ) Piperidin-4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- (2- cyanoacetyl ) piperidin -4- yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.34 (s, 1H), 10.49 (s, 1H), 7.79 (s, 1H), 7.32-7.26 (m, 1H), 6.52 (dd, J = 3.5 , 1.8 Hz, 1H), 4.54-4.46 (m, 1H), 4.10 (q, J = 18.8 Hz, 2H), 3.78 (d, J = 13.8 Hz, 1H), 3.28-3.14 (m, 3H), 2.78 (t, J = 12.6 Hz, 1H), 2.05-1.96 (m, 1H), 1.82 (dtt, J = 22.0, 13.6, 7.6 Hz, 3H), 1.60-1.47 (m, 1H), 0.78 (m, 4H ).

MS (ESI +) m / z 352 (M + H) ⁺

Example  653 N-butyl-4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) piperidine-1-carboxamide (N- butyl -4- (6- ( cyclopropanecarboxamido ) -1H-pyrrolo [2,3-b] pyridin-4-yl) piperidine-1-carboxamide)

MS (ESI +) m / z 384 (M + H) ⁺

Example 654: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -N- (2,2,2-trifluoroethyl) piperidine-1-carboxamide (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin Synthesis of -4-yl) -N- (2,2,2-trifluoroethyl) piperidine-1-carboxamide)

MS (ESI +) m / z 410 (M + H) ⁺

Example  655: tert -Butyl 4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3-hydroxypiperidine-1-carboxylate ( tert - butyl  Synthesis of 4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-hydroxypiperidine-1-carboxylate)

MS (ESI +) m / z 401 (M + H) ⁺

Example  656: tert -Butyl 4- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3-fluoropiperidine-1-carboxylate ( tert - butyl  Synthesis of 4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3-fluoropiperidine-1-carboxylate)

MS (ESI +) m / z 403 (M + H) ⁺

Example  657: N- (4- (8- ( Ethylcarbamothioyl )-8- Azabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (ethylcarbamothioyl) -8-azabicyclo [3.2.1] octan Synthesis of -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 398 (M + H) ⁺

Example  658: N- (4- (1- ( Ethylcarbamothioyl ) Piperidin-4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- ( ethylcarbamothioyl ) piperidin Synthesis of -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI < + >) m / z 372 (M + H) ⁺

Example  659: N- (4- (1- ( Butylcarbamothioyl ) Piperidin-4-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (1- ( butylcarbamothioyl ) piperidin Synthesis of -4-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.36 (s, 1H), 10.51 (s, 1H), 7.78 (s, 1H), 7.66 (t, J = 5.4 Hz, 1H), 7.29 (t, J = 2.7 Hz, 1H), 6.48 (dd, J = 1.8, 3.5 Hz, 1H), 4.89-4.75 (m, 2H), 3.51 (q, J = 6.6 Hz, 2H), 3.23 (t, J = 11.8 Hz, 1H), 3.09 (t, J = 12.9 Hz, 2H), 1.99 (d, J = 7.8 Hz, 1H), 1.83 (d, J = 12.9 Hz, 2H), 1.69-1.48 (m, 4H), 1.29 (h, J = 7.4 Hz, 2H), 0.90 (t, J = 7.3 Hz, 3H), 0.83-0.72 (m, 4H).

MS (ESI +) m / z 400 (M + H) ⁺

Example  660: N- (4- (4- ( Methylsulfonyl Piperazin-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( methylsulfonyl ) piperazin -One- yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

1 g (2.6 mmol) of the synthesized N- (4-chloro-1-tosyl-1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide was dissolved in BuOH, and 1- ( 0.6 g (3.9 mmol) of methylsulfonyl) piperazine and 1 g (5.2 mmol) of DIPEA were added and stirred at 120 to 130 ^° C. for 3 hours. When the reaction was completed, the mixture was cooled to room temperature, water was added, and then extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue. The residue was separated and concentrated on silica gel column chromatography (DCM / MeOH = 30: 1). The synthesized material was dissolved in MeOH / THF (1: 1) solution and 2N aqueous sodium hydroxide solution was added and stirred at 30-40 ^° C. for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and saturated aqueous ammonium chloride solution was added with stirring. The resulting solid was filtered to give the product N- (4- (4- (methylsulfonyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarbox Mid was obtained.

MS (ESI +) m / z 364 (M + H) ⁺

Example  661-704

Hereinafter, in Examples 661 to 704, the synthesis was carried out in the same manner as in Example 661, or synthesized using an appropriate reactant in consideration of Scheme 1 and the structure of the compound to be prepared.

Example  661: N- (4- (8- ( Methylsulfonyl ) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (methylsulfonyl) -3,8-diazabicyclo [3.2.1 ] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.15 (s, 1H), 10.32 (s, 1H), 7.35 (s, 1H), 7.11 (t, J = 3.0 Hz, 1H), 6.46 (dd, J = 3.7, 2.0 Hz, 1H), 4.30 (d, J = 4.0 Hz, 2H), 3.80 (d, J = 10.3 Hz, 2H), 3.08 (d, J = 11.9 Hz, 2H), 3.04 (s, 3H), 1.99 (s, 3H), 1.86 (d, J = 7.4 Hz, 2H), 0.82-0.71 (m, 4H).

MS (ESI +) m / z 390 (M + H) ⁺

Example  662: N- (4- (4-(((1- Cyanocyclopropyl ) methyl ) Sulfonyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4-(((1-cyanocyclopropyl)) Synthesis of methyl) sulfonyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 429 (M + H) ⁺

Example  663: N- (4- (4-((3- Fluoropropyl ) Sulfonyl) piperazin-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4-((3-fluoropropyl) sulfonyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) Synthesis of cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.21 (s, 1H), 10.39 (s, 1H), 7.43 (s, 1H), 7.16 (s, 1H), 6.43 (s, 1H), 4.61 ( t, J = 6.0 Hz, 1H), 4.49 (t, J = 6.0 Hz, 1H), 3.60 (s, 1H), 3.40 (d, J = 6.3 Hz, 5H), 3.24-3.17 (m, 2H), 2.15-1.98 (m, 3H), 1.76 (s, 1H), 0.78 (dd, J = 6.1, 11.2 Hz, 4H).

MS (ESI +) m / z 410 (M + H) ⁺

Example  664: N- (4- (8-((3- Cyanopropyl ) Sulfonyl) -3,8- Diazabicyclo [3.2.1] Octane-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8-((3-cyanopropyl) sulfonyl) -3,8 -diazabicyclo [3.2.1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.14 (s, 1H), 10.31 (s, 1H), 7.36 (s, 1H), 7.17-7.05 (m, 1H), 6.46 (dd, J = 1.9 , 3.6 Hz, 1H), 4.31 (s, 2H), 3.80 (d, J = 11.6 Hz, 2H), 3.27 (d, J = 7.7 Hz, 2H), 3.11 (d, J = 11.5 Hz, 2H), 2.72-2.64 (m, 2H), 2.04 (q, J = 7.4 Hz, 3H), 1.89 (s, 2H), 0.84-0.72 (m, 4H).

MS (ESI +) m / z 443 (M + H) ⁺

Example  665: N- (4- (8-(((1- (cyanomethyl) cyclopropyl) methyl) sulfonyl) -3,8-diazabicyclo [3.2.1] octan-3-yl) -1H- Pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8-((1- (cyanomethyl) cyclopropyl) methyl) sulfonyl) -3,8-diazabicyclo [3.2 .1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.15 (s, 1H), 10.31 (s, 1H), 7.35 (s, 1H), 7.11 (dd, J = 2.5, 3.6 Hz, 1H), 6.46 ( dd, J = 2.0, 3.6 Hz, 1H), 4.33 (s, 2H), 3.84-3.69 (m, 2H), 3.12 (d, J = 11.8 Hz, 2H), 2.83 (s, 2H), 2.00 (s , 1H), 1.89 (d, J = 3.7 Hz, 2H), 0.88-0.81 (m, 2H), 0.76 (ddt, J = 3.0, 5.1, 12.9 Hz, 4H), 0.71-0.65 (m, 2H).

MS (ESI +) m / z 469 (M + H) ⁺

Example  666: N- (4- (8-((4,4,4- Trifluorobutyl ) Sulfonyl) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8-((4,4,4-trifluorobutyl) sulfonyl) -3, Synthesis of 8-diazabicyclo [3.2.1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.15 (s, 1H), 10.31 (s, 1H), 7.35 (s, 1H), 7.11 (dd, J = 2.5, 3.6 Hz, 1H), 6.46 ( dd, J = 2.0, 3.6 Hz, 1H), 4.33 (s, 2H), 3.84-3.69 (m, 2H), 3.12 (d, J = 11.8 Hz, 2H), 2.83 (s, 2H), 2.00 (s , 1H), 1.89 (d, J = 3.7 Hz, 2H), 0.88-0.81 (m, 2H), 0.76 (ddt, J = 3.0, 5.1, 12.9 Hz, 4H), 0.71-0.65 (m, 2H).

MS (ESI +) m / z 486 (M + H) ⁺

Example  667: N- (4- (8-(((1- Cyanocyclopropyl ) methyl ) Sulfonyl) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8-(((1-cyanocyclopropyl) methyl) sulfonyl) -3,8 -diazabicyclo [3.2.1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.14 (s, 1H), 10.30 (s, 1H), 7.35 (s, 1H), 7.11 (dd, J = 2.4, 3.6 Hz, 1H), 6.45 ( dd, J = 1.9, 3.6 Hz, 1H), 4.68 (s, 1H), 4.40-4.28 (m, 1H), 3.85-3.75 (m, 1H), 3.65 (d, J = 11.2 Hz, 1H), 3.04 (dd, J = 11.3, 42.2 Hz, 2H), 2.83-2.57 (m, 2H), 1.98 (d, J = 7.0 Hz, 1H), 1.97-1.81 (m, 4H), 1.24-1.17 (m, 2H ), 1.02-0.90 (m, 2H), 0.82-0.70 (m, 4H).

MS (ESI +) m / z 455 (M + H) ⁺

Example  668: N- (4- (4- ( Propylsulfonyl Piperazin-1-yl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- ( propylsulfonyl ) piperazin -One- yl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.57 (s, 1H), 10.05 (s, 1H), 7.09 (d, J = 3.6 Hz, 1H), 6.57 (d, J = 3.6 Hz, 1H) , 4.02-3.90 (m, 4H), 3.28 (s, 4H), 3.08-3.01 (m, 2H), 2.18 (s, 1H), 1.70 (q, J = 7.5 Hz, 2H), 0.98 (t, J = 7.4 Hz, 3H), 0.81-0.72 (m, 4H).

MS (ESI +) m / z 393 (M + H) ⁺

Example  669: N- (4- (8- ( Ethylsulfonyl ) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide (N- (4- (8- (ethylsulfonyl) -3,8-diazabicyclo [3.2. 1] octan-3-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 405 (M + H) ⁺

Example  670: (R) -N- (4- (3- ( Propylsulfonamido ) Pyrrolidine -1-yl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide ((R) -N- (4- (3- (propylsulfonamido) pyrrolidin-1-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.44 (s, 1H), 9.87 (s, 1H), 7.49 (d, J = 6.4 Hz, 1H), 7.06-6.95 (m, 1H), 6.48 ( s, 1H), 4.07-3.57 (m, 7H), 3.06 (dd, J = 6.4, 9.1 Hz, 2H), 2.23 (s, 1H), 1.97 (s, 1H), 1.68 (q, J = 7.6 Hz , 2H), 1.17 (s, 2H), 0.98 (t, J = 7.4 Hz, 3H).

MS (ESI +) m / z 393 (M + H) ⁺

Example  671: (R) -N- (4- (3- ( Allylsulfon Amido ) Pyrrolidine -1-yl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide ((R) -N- (4- (3- (allylsulfonamido) pyrrolidin-1-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.45 (s, 1H), 9.89 (s, 1H), 7.62 (s, 1H), 7.05-6.97 (m, 1H), 6.53-6.42 (m, 1H ), 5.89-5.74 (m, 4H), 5.40 (t, J = 13.6 Hz, 3H), 3.94-3.85 (m, 7H), 2.23 (s, 1H), 1.94 (d, J = 28.2 Hz, 1H) , 0.80-0.73 (m, 4H).

MS (ESI +) m / z 391 (M + H) ⁺

Example  672: (R) -N- (4- (3- (N- Methylethylsulfonamido ) Pyrrolidine -1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide ((R) -N- (4- (3- (N-methylethylsulfonamido) pyrrolidin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl Synthesis of Cyclopropanecarboxamide

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.97 (s, 1H), 10.17 (s, 1H), 7.09-6.94 (m, 2H), 6.54 (dd, J = 3.6, 1.9 Hz, 1H), 4.52 (p, J = 8.0 Hz, 1H), 3.73 (t, J = 8.9 Hz, 2H), 3.56 (q, J = 8.2 Hz, 2H), 3.22-3.09 (m, 2H), 2.82 (s, 3H ), 2.18 (q, J = 8.2, 7.7 Hz, 2H), 1.99 (s, 1H), 1.22 (t, J = 7.3 Hz, 3H), 0.84-0.63 (m, 4H).

MS (ESI +) m / z 392 (M + H) ⁺

Example  673: N- (4- (4- ( Morpholinosulfonyl Piperazin-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- ( morpholinosulfonyl ) piperazin -1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.21 (s, 1H), 10.39 (s, 1H), 7.43 (s, 1H), 7.20-7.06 (m, 1H), 6.43 (dd, J = 1.9 , 3.6 Hz, 1H), 3.63 (t, J = 4.6 Hz, 4H), 3.16 (d, J = 5.1 Hz, 8H), 2.00 (s, 1H), 0.83-075 (m, 4H).

MS (ESI +) m / z 435 (M + H) ⁺

Example  674: N- (4- (4- ( N, N - Dimethyl sulfamoyl Piperazin-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (N, N-dimethylsulfamoyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.21 (s, 1H), 10.39 (s, 1H), 7.43 (s, 1H), 7.15 (t, J = 3.0 Hz, 1H), 6.43 (dd, J = 1.9, 3.6 Hz, 1H), 3.17 (d, J = 5.2 Hz, 8H), 2.81 (s, 6H), 2.00 (s, 1H), 0.85-0.70 (m, 4H).

MS (ESI +) m / z 393 (M + H) ⁺

Example  675: N- (4- (4- (2- Cyanoacetamino ) Piperidin-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- cyanoacetamido ) piperidin -1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 367 (M + H) ⁺

Example  676: N- (4- (4- (2- Cyanoacetyl Piperazin-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (2- cyanoacetyl ) piperazin -One- yl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.18 (s, 1H), 10.35 (s, 1H), 7.40 (s, 1H), 7.14 (t, J = 3.0 Hz, 1H), 6.44 (dd, J = 1.9, 3.6 Hz, 1H), 4.10 (s, 2H), 3.66 (s, 2H), 3.56 (s, 2H), 3.38 (s, 4H), 2.08 (s, 3H), 2.00 (s, 1H ), 0.82-0.73 (m, 4H).

MS (ESI +) m / z 353 (M + H) ⁺

Example  677: N- (4- (8- (2- Cyanoacetyl ) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] -cyclopropanecarboxamide (N- (4- (8- (2-cyanoacetyl) -3,8-diazabicyclo [3.2.1] octan- Synthesis of 3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.16 (s, 1H), 10.33 (s, 1H), 7.36 (s, 1H), 7.15-7.09 (m, 1H), 6.45 (dd, J = 3.8 , 2.0 Hz, 1H), 4.64 (s, 1H), 4.33 (d, J = 6.5 Hz, 1H), 4.09 (d, J = 4.5 Hz, 2H), 3.81 (d, J = 11.4 Hz, 1H), 3.65 (d, J = 11.6 Hz, 1H), 3.16 (d, J = 11.8 Hz, 1H), 2.98 (d, J = 11.4 Hz, 1H), 2.00 (q, J = 7.2 Hz, 2H), 1.90 ( d, J = 5.5 Hz, 1H), 1.87 (s, 2H), 0.82-0.72 (m, 4H).

MS (ESI +) m / z 379 (M + H) ⁺

Example  678: N- (4- (3- (2- Cyanoacetyl ) -3,8- Diazabicyclo [3.2.1] octane -8-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) -cyclopropanecarboxamide (N- (4- (3- (2-cyanoacetyl) -3,8-diazabicyclo [ 3.2.1] Synthesis of octan-8-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.16 (s, 1H), 10.33 (s, 1H), 7.39 (s, 1H), 7.17-7.09 (m, 1H), 6.50 (dd, J = 1.9 , 3.6 Hz, 1H), 4.61-4.46 (m, 2H), 4.18 (d, J = 18.9 Hz, 1H), 4.10-3.98 (m, 2H), 3.87 (d, J = 18.9 Hz, 1H), 1.97 1.84 (m, 3H), 1.27-1.14 (m, 4H), 0.77 (ddt, J = 3.1, 5.2, 10.9 Hz, 4H).

MS (ESI +) m / z 379 (M + H) ⁺

Example  679: N- (4-(( 1S, 4S ) -5- (2- Cyanoacetyl ) -2,5- Diazabicyclo [2.2.1] heptane -2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4-((1S, 4S) -5- (2-cyanoacetyl) -2 , 5-diazabicyclo [2.2.1] heptan-2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.01 (d, J = 8.5 Hz, 1H), 10.19 (s, 1H), 7.09 (s, 1H), 7.02 (ddd, J = 6.6, 3.6, 2.4 Hz, 1H), 6.43 (ddd, J = 13.9, 3.5, 1.9 Hz, 1H), 4.84-4.61 (m, 2H), 4.09-4.05 (m, 1H), 4.04-3.97 (m, 1H), 3.90- 3.72 (m, 3H), 3.56 (d, J = 28.4 Hz, 1H), 3.43 (d, J = 6.6 Hz, 1H), 3.17 (d, J = 5.1 Hz, 1H), 2.12-2.07 (m, 1H ), 1.24 (s, 1 H), 0.80-0.77 (m, 2H), 0.74 (dd, J = 7.6, 3.5 Hz, 2H).

MS (ESI +) m / z 365 (M + H) ⁺

Example  680: N- (4-(( 1S, 4S ) -5- (3- Cyanopropanoyl ) -2,5- Diazabicyclo [2.2.1] heptane 2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4-((1S, 4S) -5- (3-cyanopropanoyl) -2 , 5-diazabicyclo [2.2.1] heptan-2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.00 (s, 1H), 10.19 (s, 1H), 7.09 (s, 1H), 7.02 (td, J = 3.9, 2.4 Hz, 1H), 6.44 ( ddd, J = 6.3, 3.7, 2.0 Hz, 1H), 4.86-4.65 (m, 2H), 3.87 (d, J = 9.2 Hz, 1H), 3.68-3.48 (m, 2H), 3.43 (s, 1H) , 2.89-2.65 (m, 2H), 2.57 (dd, J = 16.5, 9.4 Hz, 2H), 2.07 (s, 1H), 0.79-0.71 (m, 4H).

MS (ESI +) m / z 379 (M + H) ⁺

Example  681: N- (4-(( 1R, 4R ) -5- (2- Cyanoacetyl ) -2,5- Diazabicyclo [2.2.1] heptane -2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4-((1R, 4R) -5- (2-cyanoacetyl) -2 , 5-diazabicyclo [2.2.1] heptan-2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.03 (d, J = 8.7 Hz, 1H), 10.22 (s, 1H), 7.09 (s, 1H), 7.03 (dt, J = 6.7, 3.1 Hz, 1H), 6.43 (d, J = 14.4 Hz, 1H), 4.83-4.60 (m, 2H), 4.08 (q, J = 18.8 Hz, 2H), 3.90-3.72 (m, 2H), 3.61-3.49 (m , 1H), 3.43 (d, J = 6.4 Hz, 1H), 2.04 (dt, J = 45.1, 6.5 Hz, 2H), 1.89 (d, J = 9.3 Hz, 1H), 0.81-0.69 (m, 4H) .

MS (ESI +) m / z 365 (M + H) ⁺

Example  682: N- (4-(( 1R, 4R ) -5- (3- Cyanopropanoyl ) -2,5- Diazabicyclo [2.2.1] heptane 2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4-((1R, 4R) -5- (3-cyanopropanoyl) -2 , 5-diazabicyclo [2.2.1] heptan-2-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.02 (s, 1H), 10.22 (s, 1H), 7.09 (s, 1H), 7.02 (q, J = 3.7 Hz, 1H), 6.43 (s, 1H), 4.84-4.66 (m, 2H), 3.87 (d, J = 9.0 Hz, 1H), 3.66-3.47 (m, 2H), 3.16 (d, J = 5.2 Hz, 2H), 2.11-1.93 (m , 4H), 1.89 (d, J = 10.0 Hz, 1H), 0.75 (ddd, J = 13.6, 6.3, 3.9 Hz, 4H).

MS (ESI +) m / z 379 (M + H) ⁺

Example  683: N- (4- (4- (2- (1- Cyanocyclopropyl ) Acetyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (1-cyanocyclopropyl)) acetyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.19 (s, 1H), 10.37 (s, 1H), 7.40 (s, 1H), 7.22-7.10 (m, 1H), 6.50-6.40 (m, 1H ), 3.68 (s, 2H), 3.56 (s, 2H), 2.73 (d, J = 6.0 Hz, 4H), 2.00 (s, 1H), 0.95-0.90 (m, 2H), 0.82-0.73 (m, 4H).

MS (ESI +) m / z 393 (M + H) ⁺

Example  684: N- (4- (4- (3- Cyanopropanoyl Piperazin-1-yl) -1H- Pyrrolo [2,3-b] Pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (3- cyanopropanoyl ) piperazin -1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.19 (s, 1H), 10.37 (s, 1H), 7.40 (s, 1H), 7.20-7.06 (m, 1H), 6.56-6.38 (m, 1H ), 3.65 (d, J = 17.9 Hz, 4H), 2.92-2.66 (m, 4H), 2.66-2.53 (m, 4H), 2.00 (s, 1H), 0.81-0.71 (m, 4H).

MS (ESI +) m / z 367 (M + H) ⁺

Example  685: N- (4- (6- (2- Cyanoacetyl ) -3,6- Diazabicyclo [3.1.1] heptane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (6- (2-cyanoacetyl) -3,6-diazabicyclo [ 3.1.1] Synthesis of heptane-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 365 (M + H) ⁺

Example  686: N- (4- (8- (3- Cyanobenzoyl ) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (3-cyanobenzoyl) -3,8-diazabicyclo [ 3.2.1] Synthesis of octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 441 (M + H) ⁺

Example  687: N- (4- (4- (2- Cyanoacetyl Piperazin-1-yl) -7H- Pyrrolo [2,3-d] pyrimidine 2-yl) cyclopropanecarboxamide (N- (4- (4- (2- cyanoacetyl ) piperazin -One- yl ) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.55 (s, 1H), 10.03 (s, 1H), 7.07 (t, J = 2.9 Hz, 1H), 6.56 (d, J = 2.8 Hz, 1H) , 4.10 (s, 2H), 3.91 (dt, J = 5.1, 19.7 Hz, 3H), 3.57 (dt, J = 5.5, 41.4 Hz, 4H), 2.20 (d, J = 10.8 Hz, 1H), 0.76 ( dt, J = 3.8, 11.0 Hz, 4H).

MS (ESI +) m / z 354 (M + H) ⁺

Example  688: N- (4- (8- (2- Cyanoacetyl ) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -7H-pyrrolo [2,3-d] pyrimidine-2-cyclopropanecarboxamide (N- (4-((8- (2-cyanoacetyl) -3,8-diazabicyclo [3.2 .1] octan-3-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 380 (M + H) ⁺

Example  689: N- (4- (8- (2- (1- Cyanocyclopropyl ) Acetyl) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide (N- (4- (8- (2- (1-cyanocyclopropyl) acetyl) -3) , 8-diazabicyclo [3.2.1] octan-3-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 420 (M + H) ⁺

Example 690: 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -N- (2,2,2-trifluoroethyl) piperazin-1-carboxamide (4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin- Synthesis of 4-yl) -N- (2,2,2-trifluoroethyl) piperazine-1-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.18 (s, 1H), 10.36 (s, 1H), 7.40 (s, 1H), 7.25 (t, J = 6.1 Hz, 1H), 7.14 (d, J = 3.5 Hz, 1H), 6.88 (s, 1H), 6.44 (s, 1H), 3.85 (dt, J = 5.9, 10.8 Hz, 4H), 3.59 (d, J = 6.6 Hz, 2H), 3.54 ( s, 4H), 2.00 (s, 1H), 0.81-0.74 (m, 4H).

MS (ESI +) m / z 411 (M + H) ⁺

Example 691: 3 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine 4-yl) -N- (2,2,2-trifluoroethyl) -3,8-diazabicyclo [3.2.1] octane-8-carboxamide (3- (6- (cyclopropanecarboxamido) Synthesis of -1H-pyrrolo [2,3-b] pyridin-4-yl) -N- (2,2,2-trifluoroethyl) -3,8-diazabicyclo [3.2.1] octane-8-carboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.13 (s, 1H), 10.30 (s, 1H), 7.33 (d, J = 6.9 Hz, 2H), 7.10 (dd, J = 2.5, 3.6 Hz, 1H), 6.45 (dd, J = 1.9, 3.6 Hz, 1H), 4.42 (s, 2H), 3.93-3.78 (m, 2H), 3.70-3.61 (m, 2H), 3.03 (d, J = 11.3 Hz , 2H), 1.99 (s, 1H), 1.86 (s, 4H), 0.83-0.71 (m, 4H).

MS (ESI +) m / z 437 (M + H) ⁺

Example  692: tert - Butyl 4 -(6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) piperazin-1-carboxylate ( tert - butyl  Synthesis of 4- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridine-4-yl) piperazin-1-carboxylate)

MS (ESI +) m / z 386 (M + H) ⁺

Example  693: tert -Butyl 3- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3,8-diazabicyclo [3.2.1] octane-8-carboxylate ( tert - butyl  Synthesis of 3- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,8-diazabicyclo [3.2.1] octane-8-carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.14 (s, 1H), 10.31 (s, 1H), 7.34 (s, 1H), 7.11 (d, J = 3.0 Hz, 1H), 6.46 (d, J = 3.1 Hz, 1H), 4.26 (d, J = 5.3 Hz, 2H), 3.71 (d, J = 11.5 Hz, 2H), 3.00 (d, J = 12.0 Hz, 2H), 1.99 (s, 1H) , 1.85 (s, 4H), 1.42 (s, 9H), 0.89-0.67 (m, 4H).

MS (ESI +) m / z 412 (M + H) ⁺

Example  694: tert -Butyl 8- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -3,8-diazabicyclo [3.2.1] octane-3-carboxylate ( tert - butyl  Synthesis of 8- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) -3,8-diazabicyclo [3.2.1] octane-3-carboxylate)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.12 (s, 1H), 10.30 (s, 1H), 7.36 (s, 1H), 7.09 (dd, J = 2.5, 3.6 Hz, 1H), 6.49 ( dd, J = 2.0, 3.7 Hz, 1H), 4.49 (s, 2H), 3.68 (t, J = 16.9 Hz, 3H), 3.42 (d, J = 10.5 Hz, 1H), 3.20-3.12 (m, 1H ), 3.02 (d, J = 12.4 Hz, 1H), 2.03-1.92 (m, 3H), 1.39 (s, 9H), 0.80-0.72 (m, 4H).

MS (ESI +) m / z 412 (M + H) ⁺

Example  695: tert -Butyl 3- (2- ( Cyclopropanecarboxamido ) -7H- Pyrrolo [2,3-d] pyrimidine -4-yl) -3,8-diazabicyclo [3.2.1] octane-8-carboxylate ( tert - butyl  Synthesis of 3- (2- (cyclopropanecarboxamido) -7H-pyrrolo [2,3-d] pyrimidin-4-yl) -3,8-diazabicyclo [3.2.1] octane-8-carboxylate)

MS (ESI +) m / z 413 (M + H) ⁺

Example  696: tert -Butyl (R)-(1- (2- ( Cyclopropanecarboxamido ) -7H- Pyrrolo [2,3-d] pyrimidine -4-yl) pyrrolidin-3-yl) carbamate ( tert - butyl  Synthesis of (R)-(1- (2- (cyclopropanecarboxamido) -7H-pyrrolo [2,3-d] pyrimidin-4-yl) pyrrolidin-3-yl) carbamate)

MS (ESI +) m / z 387 (M + H) ⁺

Example  697: tert -Butyl (R)-(1- (6- ( Cyclopropanecarboxamido ) -1H- Pyrrolo [2,3-b] pyridine -4-yl) pyrrolidin-3-yl) carbamate ( tert - butyl  Synthesis of (R)-(1- (6- (cyclopropanecarboxamido) -1H-pyrrolo [2,3-b] pyridin-4-yl) pyrrolidin-3-yl) carbamate)

MS (ESI +) m / z 386 (M + H) ⁺

Example  698: N- (4- (4- ( Isothiazole -5- Methyl Piperazin-1-yl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropanecarboxamide (N- (4- (4- (isothiazol-5-ylmethyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ) Synthesis

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.15 (s, 1H), 10.34 (s, 1H), 8.49 (d, J = 1.7 Hz, 1H), 7.39 (s, 1H), 7.31 (d, J = 1.6 Hz, 1H), 7.11 (t, J = 3.0 Hz, 1H), 6.39 (dd, J = 1.9, 3.6 Hz, 1H), 4.11 (t, J = 5.2 Hz, 1H), 3.96 (s, 2H), 3.17 (d, J = 5.2 Hz, 3H), 2.66 (t, J = 4.7 Hz, 4H), 2.00 (s, 1H), 0.82-0.74 (m, 4H).

MS (ESI +) m / z 383 (M + H) ⁺

Example  699: (S) -N- (4- (4-((2,2- Difluorocyclopropyl ) methyl Piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide ((S) -N- (4- (4-((2,2- Synthesis of difluorocyclopropyl) methyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.41 (s, 1H), 10.57 (s, 1H), 7.67 (s, 1H), 7.31 (t, J = 3.0 Hz, 1H), 6.24 (tt, J = 1.5, 3.3 Hz, 1H), 4.14 (dd, J = 1.2, 3.5 Hz, 2H), 4.07-3.94 (m, 2H), 3.70 (t, J = 5.7 Hz, 1H), 3.57 (t, J = 5.7 Hz, 1H), 2.34 (s, 1H), 2.05-1.95 (m, 1H), 1.52 (s, 3H), 1.24 (d, J = 8.3 Hz, 1H), 0.83-0.75 (m, 4H) .

MS (ESI +) m / z 376 (M + H) ⁺

Example  700: N- (4- (4- (3- ( Cyanomethyl )-One-( Ethylsulfonyl ) Azetidine -3-yl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (3- (cyanomethyl)) Synthesis of -1- (ethylsulfonyl) azetidin-3-yl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 472 (M + H) ⁺

Example  701: N- (4- (8- (3- ( Cyanomethyl )-One-( Ethylsulfonyl ) Azetidine -3-yl) -3,8- Diazabicyclo [3.2.1] octane -3-yl) -2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (3- (cyanomethyl) -1- (ethylsulfonyl) azetidin-3-yl) -3,8-diazabicyclo [3.2.1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 10.29 (s, 1H), 9.46 (s, 1H), 7.49-7.37 (m, 2H), 6.71-6.60 (m, 1H), 4.54 (d, J = 9.2 Hz, 2H), 4.24 (d, J = 9.1 Hz, 2H), 4.14 (s, 2H), 3.87-3.74 (m, 2H), 3.19 (q, J = 7.3 Hz, 2H), 2.37 (q , J = 7.4 Hz, 2H), 1.99 (s, 5H), 1.25-1.21 (m, 3H), 1.05 (t, J = 7.4 Hz, 3H), 0.82-0.74 (m, 4H).

MS (ESI +) m / z 498 (M + H) ⁺

Example  702: N- (4- (4- (2- (1,1- Deoxythiomorpholino )-2- Oxoethyl Piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (4- (2- (1,1-dioxidothiomorpholino) Synthesis of -2-oxoethyl) piperazin-1-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 461 (M + H) ⁺

Example  703: N- (4- (8- (2-((R) -2-cyanopyrrolidin-1-yl) -2-oxoethyl) -3,8-diazabicyclo [3.2.1] octane -3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide (N- (4- (8- (2-((R) -2-cyanopyrrolidin-1-1 -yl) -2-oxoethyl) -3,8-diazabicyclo [3.2.1] octan-3-yl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.49 (s, 1H), 9.96 (s, 1H), 7.01 (t, J = 2.9 Hz, 1H), 6.53 (d, J = 3.3 Hz, 1H) , 4.31 (dt, J = 8.5, 4.3 Hz, 2H), 3.74 (dt, J = 9.8, 6.3 Hz, 1H), 3.63 (s, 2H), 3.56 (s, 1H), 3.28-3.14 (m, 4H ), 2.24-2.11 (m, 2H), 1.94-1.83 (m, 4H), 1.54 (d, J = 8.7 Hz, 2H), 0.75 (qd, J = 8.5, 4.8 Hz, 4H).

MS (ESI +) m / z 448 (M + H) ⁺

Example  704: N- (4- (8- (2- (1,1-dioxythiomorpholino) -2-oxoethyl) -3,8-diazabicyclo [3.2.1] octan-3-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide (N- (4- (8- (2- (1,1-dioxidothiomorpholino) -2-oxoethyl) -3 , 8-diazabicyclo [3.2.1] octan-3-yl) -7H-pyrrolo [2,3-d] pyrimidin-2-yl) cyclopropanecarboxamide)

MS (ESI +) m / z 488 (M + H) ⁺

Example  705: (S) -3- (4- (6-amino-lH-) Pyrrolo [2,3-b] pyridine -4-yl) -3- methyl -3,6-dihydropyridin-1 (2H) -yl) -3-oxopropanenitrile ((S) -3- (4- (6-amino-1H-pyrrolo [2,3-b] pyridin-4 -yl) -3-methyl-3,6-dihydropyridin-1 (2H) -yl) -3-oxopropanenitrile)

MS (ESI +) m / z 296 (M + H) ⁺

Example  706: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopentane Carboxamide  (N- (4- (4- ( ethylsulfonamido ) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopentanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.57 (s, 1H), 10.29 (s, 1H), 9.83 (s, 1H), 8.04 (s, 1H), 7.58 (d, J = 9.0 Hz, 3H), 7.43 (s, 1H), 6.56 (s, 1H), 3.18 (q, J = 7.5 Hz, 2H), 2.97 (s, 1H), 1.85 (s, 2H), 1.69 (s, 4H), 1.55 (s, 2 H), 1.29 (t, J = 7.7 Hz, 4H).

MS (ESI +) m / z 417 (M + H) ⁺

Example  707: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclohexane Carboxamide  (N- (4- (4- ( ethylsulfonamido ) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclohexanecarboxamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.56 (s, 1H), 10.21 (s, 1H), 8.22 (s, 1H), 8.03 (s, 1H), 7.56 (s, 3H), 7.42 ( s, 2H), 6.55 (s, 1H), 3.17 (q, 2H), 2.36 (s, 1H), 1.76 (d, J = 23.4 Hz, 4H), 1.68-1.56 (m, 2H), 1.41 (d , J = 11.7 Hz, 4H), 1.29 (t, J = 7.1 Hz, 4H).

MS (ESI +) m / z 421 (M + H) ⁺

Example  708: N- (4- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) propionamide (N- (4- (4- ( ethylsulfonamido ) -3- fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) propionamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.38 (s, 1H), 10.14 (s, 1H), 7.94 (s, 1H), 7.47-7.36 (m, 1H), 7.33 (s, 1H), 7.26 (t, J = 9.0 Hz, 2H), 6.56 (s, 1H), 2.79 (q, J = 8.0 Hz, 2H), 2.41 (q, J = 7.7 Hz, 2H), 1.17 (t, 3H), 1.09 (t, J = 7.2 Hz, 3H).

MS (ESI +) m / z 433 (M + H) ⁺

Example  709: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) -2-phenylacetamide (N- (4- (4- ( ethylsulfonamido ) -3- fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) -2-phenylacetamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.71-11.50 (s, 1H), 10.58 (s, 1H), 9.81 (s, 1H), 8.00 (s, 1H), 7.56 (d, J = 10.0 Hz, 3H), 7.45 (s, 1H), 7.41-7.27 (m, 5H), 7.25 (d, J = 7.4 Hz, 1H), 6.56 (s, 1H), 3.74 (s, 2H), 3.23-3.04 (q, 2H), 1.35-1.25 (t, 3H).

MS (ESI +) m / z 494 (M + H) ⁺

Example  710: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) acetamide (N- (4- (4- ( ethylsulfonamido ) -3- fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) acetamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.58 (s, 1H), 10.34 (s, 1H), 9.79 (s, 1H), 7.99 (s, 1H), 7.65-7.48 (m, 3H), 7.46-7.36 (m, 1H), 6.55 (d, J = 3.2 Hz, 1H), 3.14 (q, 2H), 2.11 (s, 3H), 1.29 (t, 3H).

MS (ESI +) m / z 377 (M + H) ⁺

Example  711: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) isobutyramide (N- (4- (4- ( ethylsulfonamido ) -3- fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) isobutyramide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.57 (s, 1H), 10.28 (s, 1H), 9.83 (s, 1H), 8.04 (s, 1H), 7.58 (d, J = 8.1 Hz, 3H), 7.49-7.38 (m, 1H), 6.63-6.50 (m, 1H), 3.18 (q, J = 7.2 Hz, 2H), 2.85-2.71 (m, 1H), 1.29 (t, J = 7.0 Hz , 3H), 1.10 (d, J = 6.7 Hz, 6H).

MS (ESI +) m / z 405 (M + H) ⁺

Example  712: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) butyramide (N- (4- (4- ( ethylsulfonamido ) -3- fluorophenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) butyramide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.60 (s, 1H), 10.29 (s, 1H), 8.02 (s, 1H), 7.70-7.51 (m, 3H), 7.45-7.37 (m, 1H ), 6.56 (d, J = 3.4 Hz, 1H), 2.37 (q, J = 6.9 Hz, 2H), 1.62 (q, J = 7.5 Hz, 2H), 1.34-1.26 (m, 5H), 0.92 (t , J = 7.3 Hz, 3H).

MS (ESI +) m / z 405 (M + H) ⁺

Example  713: N- (4- (6-(( Cyclopropylmethyl ) Amino) -1H- Pyrrolo [2,3-b] pyridine -4-yl) -2-fluoro phenyl) Ethanesulfonamide  (N- (4- (6-(( cyclopropylmethyl ) amino ) -1H-pyrrolo [2,3-b] pyridin-4-yl) -2-fluorophenyl) ethanesulfonamide)

MS (ESI +) m / z 389 (M + H) ⁺

Example  714: (Z) -N- (4- (4- ( Ethylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) -N'-methylcyclopropane Carboxymidamide  Synthesis of ((Z) -N- (4- (4- (ethylsulfonamido) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) -N'-methylcyclopropanecarboximidamide)

MS (ESI +) m / z 398 (M + H) ⁺

Example  715: N- (4- (4- ( Ethylsulfonamido ) Phenyl) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropane Carbothioamide  (N- (4- (4- ( ethylsulfonamido ) phenyl ) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanecarbothioamide)

MS (ESI +) m / z 401 (M + H) ⁺

Example  716: N- (4- (4- ( Ethylsulfonamido ) -3- Fluorophenyl ) -1H- Pyrrolo [2,3-b] pyridine -6-yl) cyclopropane sulfonamide (N- (4- (4- ( ethylsulfonamido ) -3-fluorophenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) cyclopropanesulfonamide)

¹ H NMR (400 MHz, Chloroform-d) δ 10.37 (s, 1H), 7.77 (t, J = 8.3 Hz, 1H), 7.65-7.47 (m, 3H), 7.44-7.31 (m, 1H), 6.79 (s, 1H), 6.70-6.57 (m, 1H), 3.23 (q, J = 7.3 Hz, 2H), 2.65 (tt, J = 8.3, 4.7 Hz, 1H), 1.45 (t, J = 7.4 Hz, 3H), 0.99 (dt, J = 7.8, 3.7 Hz, 4H).

MS (ESI +) m / z 439 (M + H) ⁺

Example 717: 1 - Cyclopropyl -3- (4- (4-((1,1- Dioxidothiomorpholino ) methyl ) Phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) urea (1- cyclopropyl Synthesis of -3- (4- (4-((1,1-dioxidothiomorpholino) methyl) phenyl) -1H-pyrrolo [2,3-b] pyridin-6-yl) urea)

MS (ESI +) m / z 440 (M + H) ⁺

Example  718: N- (4- (2- (dimethylamino) -7H- Pyrrolo [2,3-d] pyrimidine -4-yl) phenyl) -3,4-difluorobenzenesulfonamide (N- (4- (2- ( dimethylamino ) -7H- pyrrolo [2,3- d] pyrimidin-4-yl) phenyl) -3,4-difluorobenzenesulfonamide)

¹ H NMR (400 MHz, Methanol-d ₄ ) δ 8.09-8.02 (m, 2H), 7.77 (ddd, J = 2.3, 7.3, 9.7 Hz, 1H), 7.66 (ddt, J = 1.8, 3.9, 8.6 Hz , 1H), 7.42 (ddd, J = 7.6, 8.7, 10.1 Hz, 1H), 7.32-7.25 (m, 2H), 7.02 (d, J = 3.6 Hz, 1H), 6.56 (d, J = 3.7 Hz, 1H), 3.23 (s, 6H).

MS (ESI +) m / z 430 (M + H) ⁺

Example  719: N- (2- Fluoro -4- (2- ( Phenylamino ) -7H- Pyrrolo [2,3-d] pyrimidine -4-yl) phenyl) ethanesulfonamide (N- (2- fluoro -4- (2- ( phenylamino ) -7H- pyrrolo [2,3- d] pyrimidin-4-yl) phenyl) ethanesulfonamide)

¹ H NMR (400 MHz, DMSO-d ₆ ) δ 11.69 (s, 1H), 9.93 (s, 1H), 9.30 (s, 1H), 8.04-7.95 (m, 2H), 7.93-7.84 (m, 2H ), 7.62 (t, J = 8.5 Hz, 1H), 7.29 (ddd, J = 1.8, 5.4, 8.5 Hz, 3H), 6.90 (dd, J = 6.8, 8.0 Hz, 1H), 6.75 (dd, J = 1.8, 3.7 Hz, 1H), 3.18 (q, J = 7.3 Hz, 2H), 1.28 (t, J = 7.3 Hz, 3H).

MS (ESI +) m / z 412 (M + H) ⁺

Example  720: N- (4- (2- ( Phenylamino ) -7H- Pyrrolo [2,3-d] pyrimidine -4-yl) phenyl) ethane sulfonamide (N- (4- (2- ( phenylamino ) -7H- pyrrolo [2,3-d] pyrimidin Synthesis of -4-yl) phenyl) ethanesulfonamide)

MS (ESI +) m / z 394 (M + H) ⁺

Example 721: 3 Oxo-3- (3- (2- ( Phenylamino ) -7H- Pyrrolo [2,3-d] pyrimidine -4-yl) -3,8-diazabicyclo [3.2.1] octan-8-yl) propanenitrile (3-oxo-3- (3- (2- (phenylamino) -7H-pyrrolo [2,3 -d] pyrimidin-4-yl) -3,8-diazabicyclo [3.2.1] octan-8-yl) propanenitrile)

MS (ESI +) m / z 388 (M + H) ⁺

Test Example  1: chemical formula 1 compound JAK1  activation Inhibitory ability  Analysis (ADP- Glo ^TM Kinase  assay)

JAK inhibition effect of the compound according to the present invention was confirmed as follows.

DMSO was used to prepare control and test substances diluted by concentration. Simultaneously dilute ATP (250 uM) and JAK substrate (JAK1, IRS-1tide 40 ng / mL) in kinase buffer (40 mM Tris-HCl pH 7.5, 20 mM MgCl ₂ , 0.5 mg / mL BSA, 50 uM DTT) It was prepared by.

In the Eppendorf tube, each test drug, Substrate, ATP and JAK enzyme were mixed at 30 ^o C and incubator for 40 minutes after mixing.

ADP-Glo ™ reagent contained in ADP-GloTM Kinase Enzyme System (Promega, USA, V9571) was added to each eppendorf tube and allowed to react for 40 minutes in a 30 ^o C incubator.

After inserting the kinase detection reagent included in the ADP-GloTM Kinase Enzyme System into the eppendorf tube, the integration time was set to 1 second using the Wallac Victor 2TM, and the luminescence was measured to analyze the JAKs phosphorylation inhibition activity. The concentration of the compound at which 50% of JAK enzyme activity inhibition occurs compared to the control group was determined by the IC50 (nM) of the inhibitor, and the results are shown in Table 1 below.

TABLE 1

Claims (8)

A compound represented by Formula 1, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof:
[Formula 1]

Where
X is CA ₃ or N,
Y is CA ₄ or N,
Z is N or NO,
A ₁ to A ₄ are each independently H or C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, C (═O) —OH, C (═O) —O—C 1 -C 6 alkyl, S (═O) ₂ -C 1 -C 6 alkyl, aryl or heteroaryl,
B ₁ is-(CH ₂ ) _m- , -C (= O)-, -C (= S)-, -C (= NR ₁ )-, -C (= O) -NR _1- , -S ( = O) ₂ -or nothing (null) {where one or more H of-(CH ₂ ) _m -can be substituted with C1-C6 alkyl, halogen or cyano, or linked together with one or more carbon atoms Can form a ring},
B ₂ is H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, 5-6 membered heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl-aryl or C 1 -C 6 alkyl-heteroaryl, wherein C 3 -C 7 One or more H of cycloalkyl, 5-6 membered heterocycloalkyl, aryl, heteroaryl, C1-C6 alkyl-aryl or C1-C6 alkyl-heteroaryl may be substituted with C1-C6 alkyl, hydroxy or halogen} ,
B ₃ is H or C 1 -C 6 alkyl,
Cyclic linker is C3-C7 cycloalkyl, C3-C7 cycloalkenyl, 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl,
C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 hydroxyalkyl, C 1 -C 6 cyanoalkyl, C 1 -C 6 haloalkyl, hydroxy, cyano, halogen, C (═O) —OH, C (═O) —O—C 1 -C 6 alkyl, S (═O) ₂ -C 1 -C 6 alkyl, aryl or heteroaryl,
Or C ₁ and C ₂ may be linked to each other through one or more carbon atoms to form a bicyclic ring or a spy ring,
D ₁ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

,

Or not blank (null) {wherein, - (CH _{2) m} - or _{- (CH 2) m -NR 1} - one or more H, C1-C6 alkyl, halogen or cyano and may be substituted, or one or more of Can be linked together with carbon atoms to form a ring,

or

At least one H may be substituted with C 1 -C 6 alkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl or C 1 -C 6 cyanoalkyl,
D ₂ is -C (= O)-, -C (= O) -CH ₂ -C (= O)-, -C (= S)-, -S (= O) ₂ -or nothing (null ) {Where one or more H of —C (═O) —CH ₂ —C (═O) — may be substituted with C 1 -C 6 alkyl or halogen},
D ₃ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

Or not blank (null) {wherein, - (CH _{2) m} - or _{- (CH 2) m -NR 1} - one or more H, C1-C6 alkyl, halogen or cyano and may be substituted, or one or more of Together with carbon atoms to form a ring},
D ₄ is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, S (= 0) ₂ -C ₁ -C6 alkyl, C3-C7 cycloalkyl,

, Aryl or heteroaryl
Wherein one or more H of C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl or C 1 -C 6 cyanoalkyl is C 3 -C 7 cycloalkyl Can be substituted,
C3-C7cycloalkyl or

At least one H may be substituted with C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, cyano, halogen, —C (═O) —R ₄ or —C (═O) —OR ₄ Can,
One or more H of aryl or heteroaryl is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 cyanoalkyl, C 1 -C 6 thioalkyl, hydroxy, cyano , Nitro, halogen, -C (= 0) -R ₄ , -C (= 0) -NR ₁ -R ₄ , -S (= 0) ₂ -R ₄ , -S (= 0) ₂ -NR _1- R ₄ , -NR ₁ -R ₅ ,

, May be substituted with aryl or heteroaryl [wherein

At least one H may be substituted with C 1 -C 6 alkyl or (═O)]},
R ₁ and R ₂ are each independently H or C 1 -C 6 alkyl,
R ₃ is H, C 1 -C 6 alkyl, —C (═O) —R ₄ , —C (═O) —OR ₄ , —S (═O) ₂ —R ₄ or —S (═O) ₂ -NR ₁ -R ₄ and {where W is -O-, -C (= O)-or -S (= O) ₂ -then R ₃ is nothing (null)},
R ₄ is H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R ₅ is H, C 1 -C 6 alkyl,

, Aryl or heteroaryl, wherein

At least one H may be substituted with C 1 -C 6 alkyl or (═O) and at least one H of aryl or heteroaryl may be substituted with C 1 -C 6 alkyl or halogen.
V is -CH- or -N-,
W is -CH-, -N-, -O-, -S-, -C (= 0)-, -S (= 0)-or -S (= 0) ₂ -where V is -CH If-W is not -CH-},
a to d are each independently 1, 2 or 3,
m is 1, 2 or 3. The method of claim 1,
X is CA ₃ or N,
Y is CA ₄ or N,
Z is N or NO,
A ₁ to A ₄ are each independently H or C 1 -C 6 alkyl or C 1 -C 6 cyanoalkyl,
B ₁ is-(CH ₂ ) _m- , -C (= O)-, -C (= S)-, -C (= NR ₁ )-, -C (= O) -NR _1- , -S ( = O) ₂ -or nothing (null) {where one or more H of-(CH ₂ ) _m -can be substituted with C1-C6 alkyl, halogen or cyano, or linked together with one or more carbon atoms Can form a ring},
B ₂ is H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, aryl, heteroaryl or C 1 -C 6 alkyl-aryl, wherein one of C 3 -C 7 cycloalkyl, aryl, heteroaryl or C 1 -C 6 alkyl-aryl Or more H may be substituted with C1-C6 alkyl},
B ₃ is H or C 1 -C 6 alkyl,
Cyclic linker is C3-C7 cycloalkyl, C3-C7 cycloalkenyl, 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl,
C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl, C 1 -C 6 haloalkyl, hydroxy, cyano, halogen, C (═O) —OH, C (═O) —O—C 1 -C 6 alkyl Or aryl,
Or C ₁ and C ₂ may be linked to each other through one or more carbon atoms to form a bicyclic ring or a spy ring,
D ₁ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

,

Or none (null) {where one or more H of — (CH ₂ ) _m — or — (CH ₂ ) _m —NR ₁ — may be substituted with C 1 -C 6 alkyl or halogen, or one or more carbon atoms Together with each other to form a ring,

,

or

At least one H may be substituted with C 1 -C 6 alkyl or C 1 -C 6 cyanoalkyl},
D ₂ is -C (= O)-, -C (= O) -CH ₂ -C (= O)-, -C (= S)-, -S (= O) ₂ -or nothing (null ) Wherein one or more H of —C (═O) —CH ₂ —C (═O) — may be substituted with C 1 -C 6 alkyl},
D ₃ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

Or not blank (null) {wherein, - (CH _{2) m} - or _{- (CH 2) m -NR 1} - that one or more of H is cyano may be substituted},
D ₄ is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, S (= 0) ₂ -C ₁ -C6 alkyl, C3-C7 cycloalkyl,

, Aryl or heteroaryl
Wherein one or more H of C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl or C 1 -C 6 cyanoalkyl is C 3 -C 7 cycloalkyl Can be substituted,
C3-C7cycloalkyl or

At least one H may be substituted with C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, cyano, halogen or —C (═O) —OR ₄ ,
One or more H of aryl or heteroaryl is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 thioalkyl, hydroxy, cyano, nitro, halogen, -C (= 0) -R ₄ , -C (= 0) -NR ₁ -R ₄ , -S (= 0) ₂ -R ₄ , -S (= 0) ₂ -NR ₁ -R ₄ , -NR ₁ -R ₅ or

Can be substituted with [In this case,

At least one H may be substituted with (= O)]},
R ₁ and R ₂ are each independently H or C 1 -C 6 alkyl,
R ₃ is H, C 1 -C 6 alkyl, —C (═O) —R ₄ , —C (═O) —OR ₄ , —S (═O) ₂ —R ₄ or —S (═O) ₂ -NR ₁ -R ₄ and {where W is -O-, -C (= O)-or -S (= O) ₂ -then R ₃ is nothing (null)},
R ₄ is H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R ₅ is H,

Or aryl, where {

At least one H may be substituted with (═O) and at least one H of aryl or heteroaryl may be substituted with C 1 -C 6 alkyl or halogen},
V is -CH- or -N-,
W is -CH-, -N-, -O-, -S-, -C (= 0)-, -S (= 0)-or -S (= 0) ₂ -where V is -CH If-W is not -CH-},
a to d are each independently 1, 2 or 3,
m is 1 or 2,
Compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof. The method of claim 2,
X is CA ₃ ,
Y is CA ₄ ,
Z is N or NO,
A ₁ to A ₄ are each independently H or C 1 -C 6 alkyl or C 1 -C 6 cyanoalkyl,
B ₁ is-(CH ₂ ) _m- , -C (= O)-, -C (= S)-, -C (= NR ₁ )-, -C (= O) -NR _1- , -S ( = O) ₂ -or nothing (null),
B ₂ is H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, aryl, heteroaryl or C 1 -C 6 alkyl-aryl, wherein one of C 3 -C 7 cycloalkyl, aryl, heteroaryl or C 1 -C 6 alkyl-aryl Or more H may be substituted with C1-C6 alkyl},
B ₃ is H,
Cyclic linker is C3-C7 cycloalkyl, C3-C7 cycloalkenyl, 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl,
C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl, C 1 -C 6 haloalkyl, hydroxy, cyano, halogen, C (═O) —OH, C (═O) —O—C 1 -C 6 alkyl , Or aryl,
Or C ₁ and C ₂ may be linked to each other through one or more carbon atoms to form a bicyclic ring or a spy ring,
D ₁ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

,

Or none (null) {where one or more H of — (CH ₂ ) _m — or — (CH ₂ ) _m —NR ₁ — may be substituted with C 1 -C 6 alkyl or halogen, or one or more carbon atoms Together with each other to form a ring,

,

or

At least one H may be substituted with C 1 -C 6 alkyl or C 1 -C 6 cyanoalkyl},
D ₂ is -C (= O)-, -C (= O) -CH ₂ -C (= O)-, -C (= S)-, -S (= O) ₂ -or nothing (null ) Wherein one or more H of —C (═O) —CH ₂ —C (═O) — may be substituted with C 1 -C 6 alkyl},
D ₃ is-(CH ₂ ) _m -,-(CH ₂ ) _m -NR _1- , -NR _1- , -O-,

Or not blank (null) {wherein, - (CH _{2) m} - or _{- (CH 2) m -NR 1} - that one or more of H is cyano may be substituted},
D ₄ is H, C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, S (═O) ₂ -C 1 -C 6 alkyl, C 3 -C 7 Cycloalkyl,

, Aryl or heteroaryl
Wherein one or more H of C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 alkoxyalkyl, C 1 -C 6 haloalkyl or C 1 -C 6 cyanoalkyl may be substituted with C 3 -C 7 cycloalkyl,
C3-C7cycloalkyl or

At least one H may be substituted with C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, cyano, halogen or —C (═O) —OR ₄ ,
One or more H of aryl or heteroaryl is C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 thioalkyl, hydroxy, cyano, nitro, halogen, -C (= 0) -R ₄ , -C (= 0) -NR ₁ -R ₄ , -S (= 0) ₂ -R ₄ , -S (= 0) ₂ -NR ₁ -R ₄ , -NR ₁ -R ₅ or

Can be substituted with [In this case,

At least one H may be substituted with (= O)]},
R ₁ and R ₂ are each independently H or C 1 -C 6 alkyl,
R ₃ is H, C 1 -C 6 alkyl, —C (═O) —R ₄ , —C (═O) —OR ₄ , —S (═O) ₂ —R ₄ or —S (═O) ₂ -NR ₁ -R ₄ and {where W is -O-, -C (= O)-or -S (= O) ₂ -then R ₃ is nothing (null)},
R ₄ is H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl,
R ₅ is H,

Or aryl, where {

At least one H may be substituted with (═O) and at least one H of aryl or heteroaryl may be substituted with C 1 -C 6 alkyl or halogen},
V is -CH- or -N-,
W is -CH-, -N-, -O-, -S-, -C (= 0)-, -S (= 0)-or -S (= 0) ₂ -where V is -CH If-W is not -CH-},
a to d are each independently 1, 2 or 3,
m is 1 or 2,
Compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof. The method of claim 1,
X is CA ₃ ,
Y is N,
Z is N,
A ₁ to A ₃ are each independently H or C 1 -C 6 alkyl,
B ₁ is -C (= 0)-
B ₂ is C 3 -C 7 cycloalkyl or aryl, wherein one or more H of C 3 -C 7 cycloalkyl or aryl may be substituted with C 1 -C 6 alkyl;
B ₃ is H or C 1 -C 6 alkyl,
Cyclic linker is 5-6 membered heterocycloalkyl, 5-6 membered heterocycloalkenyl, aryl or heteroaryl
C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl or halogen,
Or C ₁ and C ₂ may be linked to each other through one or more carbon atoms to form a bicyclic ring,
D ₁ is-(CH ₂ ) _m- , -NR ₁ -or nothing (null),
D ₂ is -C (= O)-, -C (= S)-, -S (= O) ₂ -or nothing (null),
D ₃ is-(CH ₂ ) _m- , -NR _1- , -O- or nothing (null),
D ₄ is C 1 -C 6 alkyl, C 1 -C 6 alkenyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, C 3 -C 7 cycloalkyl,

, Aryl or heteroaryl
{Wherein C3-C7cycloalkyl or

At least one H may be substituted with C1-C6 alkyl or cyano,
One or more H of aryl or heteroaryl may be substituted by C ₁ -C 6 alkyl, cyano, halogen or —C (═O) —NR ₁ —R ₄ },
R ₁ is H or C ₁ -C 6 alkyl,
R ₄ is H,
V is -CH- or -N-,
W is -O- or -S (= O) _2- ,
a and b are each independently 1, 2 or 3,
m is 1 or 2,
Compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof. The method of claim 2,
X is N,
Y is CA ₄ ,
Z is N,
A ₁ , A ₂ and A ₄ are each independently H or C 1 -C 6 alkyl,
B ₁ is -C (= 0)-
B ₂ is C 3 -C 7 cycloalkyl, wherein one or more H of C 3 -C 7 cycloalkyl can be substituted with C 1 -C 6 alkyl,
B ₃ is H,
Cyclic linker is aryl
C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl or halogen,
D ₁ is-(CH ₂ ) _m -or -NR _1- ,
D ₂ is -S (= O) ₂ -or nothing (null),
D ₃ is nothing (null),
D ₄ is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or heteroaryl
Wherein one or more H of C 1 -C 6 alkyl or C 1 -C 6 haloalkyl may be substituted with C 3 -C 7 cycloalkyl,
At least one H of heteroaryl may be substituted with C 1 -C 6 alkyl},
R ₁ is H,
m is 1 or 2,
Compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof. The method of claim 2,
X is N,
Y is N,
Z is N,
A ₁ and A ₂ are each independently H or C 1 -C 6 alkyl,
B ₁ is -C (= 0)-
B ₂ is C 3 -C 7 cycloalkyl, wherein one or more H of C 3 -C 7 cycloalkyl can be substituted with C 1 -C 6 alkyl,
B ₃ is H,
Cyclic linker is aryl
C ₁ and C ₂ are each independently H, C ₁ -C 6 alkyl or halogen,
D ₁ is-(CH ₂ ) _m , -NR _1- , -NR ₁ -or -O-,
D ₂ is -S (= O) ₂ -or nothing (null),
D ₃ is nothing (null),
D ₄ is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl,

, Aryl or heteroaryl
Wherein one or more H of C 1 -C 6 alkyl or C 1 -C 6 haloalkyl may be substituted with C 3 -C 7 cycloalkyl,
One or more H of aryl or heteroaryl may be substituted with cyano or halogen},
R ₁ is H,
V is -N-,
W is -O- or -S (= O) _2- ,
a and b are each independently 1, 2 or 3,
m is 1 or 2,
Compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof. The compound according to claim 1, a stereoisomer or a pharmaceutically acceptable salt thereof, which is any one selected from the group consisting of:

A pharmaceutical for preventing or treating cancer, autoimmune diseases, neurological diseases, metabolic diseases or infections comprising the compound of any one of claims 1 to 7, a stereoisomer thereof or a pharmaceutically acceptable salt thereof as an active ingredient. Composition.