TWI461423B - 用於治療Pim激酶相關病狀及疾病之噻唑啶二酮化合物 - Google Patents

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Publication number

TWI461423B

TWI461423B TW098122261A TW98122261A TWI461423B TW I461423 B TWI461423 B TW I461423B TW 098122261 A TW098122261 A TW 098122261A TW 98122261 A TW98122261 A TW 98122261A TW I461423 B TWI461423 B TW I461423B

Authority

TW

Taiwan

Prior art keywords

dione

thiazolidin

benzylidene

chloro

pyrrolidin

Prior art date

2008-07-02

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• 108091000080 Phosphotransferase Proteins 0.000 title claims description 19
• 102000020233 phosphotransferase Human genes 0.000 title claims description 19
• 238000011282 treatment Methods 0.000 title claims description 8
• 201000010099 disease Diseases 0.000 title description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 7
• 150000001467 thiazolidinediones Chemical class 0.000 title 1
• -1 (piperazin-1-yl)-5-(trifluoromethyl)benzylidene Chemical group 0.000 claims description 186
• 150000001875 compounds Chemical class 0.000 claims description 94
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 92
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 81
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 42
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 32
• 206010028980 Neoplasm Diseases 0.000 claims description 24
• 201000011510 cancer Diseases 0.000 claims description 22
• 150000001412 amines Chemical class 0.000 claims description 20
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 18
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 8
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 7
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 5
• 150000002576 ketones Chemical class 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• MAXWYVPUCAYEHZ-ZSOIEALJSA-N (5z)-5-[[5-amino-2-[3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N(C)C)CCN1C1=CC=C(N)C=C1\C=C/1C(=O)NC(=O)S\1 MAXWYVPUCAYEHZ-ZSOIEALJSA-N 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
• FAKIMWQMJWWTMG-WMZJFQQLSA-N (5z)-5-[(2-amino-4,5-dimethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC(N)=C1\C=C/1C(=O)NC(=O)S\1 FAKIMWQMJWWTMG-WMZJFQQLSA-N 0.000 claims 1
• QMQYGDZSNITFMM-WJDWOHSUSA-N (5z)-5-[[2-(4-butyl-1,4-diazepan-1-yl)-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCCC)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 QMQYGDZSNITFMM-WJDWOHSUSA-N 0.000 claims 1
• XRTACHMSFORDBV-PTNGSMBKSA-N (5z)-5-[[2-(4-propan-2-ylpiperazin-1-yl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C(C)C)CCN1C1=CC=CC=C1\C=C/1C(=O)NC(=O)S\1 XRTACHMSFORDBV-PTNGSMBKSA-N 0.000 claims 1
• ACBLHHDMVMZOHV-ZROIWOOFSA-N (5z)-5-[[2-(4-tert-butylpiperazin-1-yl)-3-chloro-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C(C)(C)C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 ACBLHHDMVMZOHV-ZROIWOOFSA-N 0.000 claims 1
• MCUJKPPARUPFJM-UWCCDQBKSA-N (5z)-5-[[2-[(3r)-3-aminopiperidin-1-yl]-3-phenylphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N)CCCN1C(C(=CC=C1)C=2C=CC=CC=2)=C1\C=C/1C(=O)NC(=O)S\1 MCUJKPPARUPFJM-UWCCDQBKSA-N 0.000 claims 1
• RFWKTXMQECDWFN-FGLUKDLVSA-N (5z)-5-[[2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-3-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](C)N[C@@H](C)C1)N1C=1C(OC)=CC=CC=1\C=C1/SC(=O)NC1=O RFWKTXMQECDWFN-FGLUKDLVSA-N 0.000 claims 1
• YNJMQRMAZKRLRC-CJAAZZPWSA-N (5z)-5-[[2-[(3s)-3-(3-aminopropylamino)pyrrolidin-1-yl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](NCCCN)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 YNJMQRMAZKRLRC-CJAAZZPWSA-N 0.000 claims 1
• APZRZCMPQNMJBG-OLWAXZHHSA-N (5z)-5-[[2-[(3s)-3-(3-aminopropylamino)pyrrolidin-1-yl]-4,5-dimethoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](CC1)NCCCN)N1C=1C=C(OC)C(OC)=CC=1\C=C1/SC(=O)NC1=O APZRZCMPQNMJBG-OLWAXZHHSA-N 0.000 claims 1
• AAILAQAKZGXUBW-GRRFOWRYSA-N (5z)-5-[[2-[(3s)-3-(3-aminopropylamino)pyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](NCCCN)CCN1C1=CC=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 AAILAQAKZGXUBW-GRRFOWRYSA-N 0.000 claims 1
• UDLTULIYJCLOJF-CJAAZZPWSA-N (5z)-5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-3-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@H](CC1)N(C)C)N1C=1C(OC)=CC=CC=1\C=C1/SC(=O)NC1=O UDLTULIYJCLOJF-CJAAZZPWSA-N 0.000 claims 1
• GSCZVAZFVSJNDT-OGGBREFQSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-(2,2,2-trifluoroethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(OCC(F)(F)F)C=CC=C1\C=C/1C(=O)NC(=O)S\1 GSCZVAZFVSJNDT-OGGBREFQSA-N 0.000 claims 1
• LPJHRWXRKNBEMC-CJAAZZPWSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-(2-methoxyethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](N)CC1)N1C=1C(OCCOC)=CC=CC=1\C=C1/SC(=O)NC1=O LPJHRWXRKNBEMC-CJAAZZPWSA-N 0.000 claims 1
• LRGBUXCKVLHMRX-ISAHRAOESA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-bromophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(Br)C=CC=C1\C=C/1C(=O)NC(=O)S\1 LRGBUXCKVLHMRX-ISAHRAOESA-N 0.000 claims 1
• GLKNPJPYEADSPB-BZPKPHBRSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-3-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C([C@@H](N)CC1)N1C=1C(OC)=CC=CC=1\C=C1/SC(=O)NC1=O GLKNPJPYEADSPB-BZPKPHBRSA-N 0.000 claims 1
• NLQUZLBPOZVPHA-IUIMMGEKSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-4-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=CC(Cl)=CC=C1\C=C/1C(=O)NC(=O)S\1 NLQUZLBPOZVPHA-IUIMMGEKSA-N 0.000 claims 1
• WNCRPWUPVGLNLK-OGGBREFQSA-N (5z)-5-[[2-[(3s)-3-aminopyrrolidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=CC=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 WNCRPWUPVGLNLK-OGGBREFQSA-N 0.000 claims 1
• AROBWOUPOTVXCM-PTNGSMBKSA-N (5z)-5-[[2-[2-(diethylamino)ethoxy]-5-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CCN(CC)CCOC1=CC=C(OC)C=C1\C=C/1C(=O)NC(=O)S\1 AROBWOUPOTVXCM-PTNGSMBKSA-N 0.000 claims 1
• VAAWBALKTIGNHB-KAMYIIQDSA-N (5z)-5-[[2-[4-(2-aminoethyl)piperazin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCN)CCN1C1=CC=CC=C1\C=C/1C(=O)NC(=O)S\1 VAAWBALKTIGNHB-KAMYIIQDSA-N 0.000 claims 1
• NVGXMUCQTFHBIC-WQLSENKSSA-N (5z)-5-[[2-piperazin-1-yl-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S\1C(=O)NC(=O)C/1=C/C1=CC(C(F)(F)F)=CC=C1N1CCNCC1 NVGXMUCQTFHBIC-WQLSENKSSA-N 0.000 claims 1
• SPIKHWFAEGMMHR-GHXNOFRVSA-N (5z)-5-[[3-chloro-2-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 SPIKHWFAEGMMHR-GHXNOFRVSA-N 0.000 claims 1
• SNMVUVIOJOQAHG-YBEGLDIGSA-N (5z)-5-[[3-chloro-2-(4-pyrrolidin-1-ylpiperidin-1-yl)-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S\1C(=O)NC(=O)C/1=C/C1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCC1N1CCCC1 SNMVUVIOJOQAHG-YBEGLDIGSA-N 0.000 claims 1
• STVUNYMVAGCJLS-OKSBFYSISA-N (5z)-5-[[3-chloro-2-[(3r)-3-(dipropylamino)piperidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@H](N(CCC)CCC)CCCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 STVUNYMVAGCJLS-OKSBFYSISA-N 0.000 claims 1
• MTVPEATYEWQMKH-LFTLCWSBSA-N (5z)-5-[[3-chloro-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=C(Cl)C=CC=C1\C=C/1C(=O)NC(=O)S\1 MTVPEATYEWQMKH-LFTLCWSBSA-N 0.000 claims 1
• RLUWZNJWIKLKCP-ZROIWOOFSA-N (5z)-5-[[3-chloro-2-[4-(2-hydroxyethyl)-1,4-diazepan-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCO)CCCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 RLUWZNJWIKLKCP-ZROIWOOFSA-N 0.000 claims 1
• SDMSSSNUMQIPGL-JYRVWZFOSA-N (5z)-5-[[3-chloro-2-[4-(2-hydroxyethyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCO)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 SDMSSSNUMQIPGL-JYRVWZFOSA-N 0.000 claims 1
• RZBQYBODURYYCR-ZSOIEALJSA-N (5z)-5-[[3-chloro-2-[4-(2-hydroxyethyl)piperidin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CC(CCO)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 RZBQYBODURYYCR-ZSOIEALJSA-N 0.000 claims 1
• KGOAOQWVVJTDQT-NVNXTCNLSA-N (5z)-5-[[3-chloro-2-[4-(2-methylpropyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CC(C)C)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 KGOAOQWVVJTDQT-NVNXTCNLSA-N 0.000 claims 1
• LEVWFFKJNVUTMF-ZROIWOOFSA-N (5z)-5-[[3-chloro-2-[4-(3-hydroxypropyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1CN(CCCO)CCN1C1=C(Cl)C=C(C(F)(F)F)C=C1\C=C/1C(=O)NC(=O)S\1 LEVWFFKJNVUTMF-ZROIWOOFSA-N 0.000 claims 1
• GHWDQWIMBBQROR-NVNXTCNLSA-N (5z)-5-[[3-chloro-2-[4-(cyclopropylmethyl)piperazin-1-yl]-5-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S\1C(=O)NC(=O)C/1=C/C1=CC(C(F)(F)F)=CC(Cl)=C1N(CC1)CCN1CC1CC1 GHWDQWIMBBQROR-NVNXTCNLSA-N 0.000 claims 1
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims 1
• GAHMOOOPIAAIJZ-UHFFFAOYSA-N 5-[[2-(3-aminopropoxy)-5-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=C(OCCCN)C(C=C2C(NC(=O)S2)=O)=C1 GAHMOOOPIAAIJZ-UHFFFAOYSA-N 0.000 claims 1
• TYDHOLYQNCKTJR-ZDUSSCGKSA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-4-methylphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC(C)=CC=C1C=C1C(=O)NC(=O)S1 TYDHOLYQNCKTJR-ZDUSSCGKSA-N 0.000 claims 1
• ZBFCRJCZTNEIOW-LBPRGKRZSA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-fluorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(F)C=C1C=C1C(=O)NC(=O)S1 ZBFCRJCZTNEIOW-LBPRGKRZSA-N 0.000 claims 1
• HGDRAPHCOZVBTC-LBPRGKRZSA-N 5-[[2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-5-methoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC(OC)=CC=C1N1CC[C@H](N(C)C)C1 HGDRAPHCOZVBTC-LBPRGKRZSA-N 0.000 claims 1
• GQZNMLNYZBPJEJ-LBPRGKRZSA-N 5-[[5-bromo-2-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(Br)C=C1C=C1C(=O)NC(=O)S1 GQZNMLNYZBPJEJ-LBPRGKRZSA-N 0.000 claims 1
• MZMOEKLRSIIVAX-UHFFFAOYSA-N 5-[[5-methoxy-2-[3-(propan-2-ylamino)propoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound COC1=CC=C(OCCCNC(C)C)C(C=C2C(NC(=O)S2)=O)=C1 MZMOEKLRSIIVAX-UHFFFAOYSA-N 0.000 claims 1
• SGIZECXZFLAGBW-UHFFFAOYSA-N 5-benzylidene-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1=CC1=CC=CC=C1 SGIZECXZFLAGBW-UHFFFAOYSA-N 0.000 claims 1
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
• RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims 1
• ATHWHSAQWLJMQO-UHFFFAOYSA-N piperidine;1,3-thiazolidine-2,4-dione Chemical compound C1CCNCC1.O=C1CSC(=O)N1 ATHWHSAQWLJMQO-UHFFFAOYSA-N 0.000 claims 1
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
• 125000003944 tolyl group Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 description 96
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
• 125000000217 alkyl group Chemical group 0.000 description 76
• 239000000203 mixture Substances 0.000 description 70
• 125000003118 aryl group Chemical group 0.000 description 41
• 235000019439 ethyl acetate Nutrition 0.000 description 38
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• 125000000623 heterocyclic group Chemical group 0.000 description 32
• 229910052736 halogen Inorganic materials 0.000 description 29
• 150000002367 halogens Chemical class 0.000 description 29
• 239000007858 starting material Substances 0.000 description 27
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
• 229910052757 nitrogen Inorganic materials 0.000 description 25
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 24
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 21
• 239000001257 hydrogen Substances 0.000 description 21
• 229910052739 hydrogen Inorganic materials 0.000 description 21
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 20
• 125000003545 alkoxy group Chemical group 0.000 description 19
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 19
• 238000006243 chemical reaction Methods 0.000 description 18
• 239000000047 product Substances 0.000 description 18
• 125000002837 carbocyclic group Chemical group 0.000 description 17
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