JP4409938B2 - アザインドール - Google Patents

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Publication number

JP4409938B2

JP4409938B2 JP2003507091A JP2003507091A JP4409938B2 JP 4409938 B2 JP4409938 B2 JP 4409938B2 JP 2003507091 A JP2003507091 A JP 2003507091A JP 2003507091 A JP2003507091 A JP 2003507091A JP 4409938 B2 JP4409938 B2 JP 4409938B2

Authority

JP

Japan

Prior art keywords

pyrrolo

methyl

indol

methoxy

pyridin

Prior art date

2001-06-21

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 471
• -1 methoxy, 4-fluorophenyl Chemical group 0.000 claims description 274
• 150000003839 salts Chemical class 0.000 claims description 72
• 229910052739 hydrogen Inorganic materials 0.000 claims description 70
• 239000001257 hydrogen Substances 0.000 claims description 56
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
• 150000001204 N-oxides Chemical class 0.000 claims description 44
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 42
• 239000012453 solvate Substances 0.000 claims description 38
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
• 150000004677 hydrates Chemical class 0.000 claims description 24
• 125000001041 indolyl group Chemical group 0.000 claims description 21
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 20
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 15
• 150000001408 amides Chemical class 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• XCLJFTFBHKDRHP-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(O)=O XCLJFTFBHKDRHP-UHFFFAOYSA-N 0.000 claims description 10
• LIZDNKRMTCXMAV-UHFFFAOYSA-N 3-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-2-yl]-1-methylindole-5-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC=NC2=C1C=C(C=1C3=CC(=CC=C3N(C)C=1)C(O)=O)N2 LIZDNKRMTCXMAV-UHFFFAOYSA-N 0.000 claims description 8
• CBSWBKLIQDUSCA-UHFFFAOYSA-N 3-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-1h-pyrrolo[2,3-b]pyridin-2-yl]-1h-indole-5-carboxylic acid Chemical compound CC1=NOC(C)=C1C1=CC=NC2=C1C=C(C=1C3=CC(=CC=C3NC=1)C(O)=O)N2 CBSWBKLIQDUSCA-UHFFFAOYSA-N 0.000 claims description 8
• CYGVUQDIFRECJA-UHFFFAOYSA-N 4-[2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2C=1C(C)=NOC=1C CYGVUQDIFRECJA-UHFFFAOYSA-N 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• AMECZOITPGYJEM-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(=O)NC(C)(C)CO AMECZOITPGYJEM-UHFFFAOYSA-N 0.000 claims description 6
• JJTVNLBIXOXIQR-UHFFFAOYSA-N 4-[2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-3,5-dimethyl-1,2-oxazole Chemical compound C12=CC(OC)=CC=C2NC=C1C(NC1=NC=C2)=CC1=C2C=1C(C)=NOC=1C JJTVNLBIXOXIQR-UHFFFAOYSA-N 0.000 claims description 5
• QPQYJHKPANJWSN-UHFFFAOYSA-N 2-(1-ethyl-5-methoxyindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C12=CC(OC)=CC=C2N(CC)C=C1C1=CC2=C(C(O)=O)C=CN=C2N1 QPQYJHKPANJWSN-UHFFFAOYSA-N 0.000 claims description 4
• QYYUOCTXNHRPHN-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-n-(2-methoxyphenyl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NC1=CC=CC=C1OC QYYUOCTXNHRPHN-UHFFFAOYSA-N 0.000 claims description 4
• 229910014033 C-OH Inorganic materials 0.000 claims description 4
• 229910014570 C—OH Inorganic materials 0.000 claims description 4
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 4
• NZQQUAQJNADKMN-UHFFFAOYSA-N n-(2-hydroxy-2-methylpropyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(=O)NCC(C)(C)O NZQQUAQJNADKMN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• IHMYLNCEAZWLKI-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(=O)NCCO IHMYLNCEAZWLKI-UHFFFAOYSA-N 0.000 claims description 3
• QXSNZHAWKYWAKB-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1C(=O)NCC(C)O QXSNZHAWKYWAKB-UHFFFAOYSA-N 0.000 claims description 3
• PYMIITKZQGMEBF-UHFFFAOYSA-N n-(2-methoxyethyl)-2-(5-methoxy-1h-indol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=C(OC)C=C2C(C=3NC=4N=CC=C(C=4C=3)C(=O)NCCOC)=CNC2=C1 PYMIITKZQGMEBF-UHFFFAOYSA-N 0.000 claims description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• LTFUDAWTAOIQCP-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-4-piperidin-1-yl-1h-pyrrolo[2,3-b]pyridine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2N1CCCCC1 LTFUDAWTAOIQCP-UHFFFAOYSA-N 0.000 claims description 2
• YKOZAXNYUUUUGV-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-n-(2-methylphenyl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NC1=CC=CC=C1C YKOZAXNYUUUUGV-UHFFFAOYSA-N 0.000 claims description 2
• GQUOQYMVODOWJW-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-n-(3-methoxyphenyl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound COC1=CC=CC(NC=2C=3C=C(NC=3N=CC=2)C=2C3=CC(OC)=CC=C3N(C)C=2)=C1 GQUOQYMVODOWJW-UHFFFAOYSA-N 0.000 claims description 2
• HFGVNZBYHIWWFF-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-n-(3-methylphenyl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NC1=CC=CC(C)=C1 HFGVNZBYHIWWFF-UHFFFAOYSA-N 0.000 claims description 2
• PSGCOJYPJYTLMY-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-n-(4-methoxyphenyl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C1=CC(OC)=CC=C1NC1=CC=NC2=C1C=C(C=1C3=CC(OC)=CC=C3N(C)C=1)N2 PSGCOJYPJYTLMY-UHFFFAOYSA-N 0.000 claims description 2
• DEUZHMAECLRWHP-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-n-(4-methylphenyl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NC1=CC=C(C)C=C1 DEUZHMAECLRWHP-UHFFFAOYSA-N 0.000 claims description 2
• DIJJUHWPCLPQPG-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-n-[(4-methoxyphenyl)methyl]-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C1=CC(OC)=CC=C1CNC1=CC=NC2=C1C=C(C=1C3=CC(OC)=CC=C3N(C)C=1)N2 DIJJUHWPCLPQPG-UHFFFAOYSA-N 0.000 claims description 2
• NXWDZEUHBORAJK-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-3-yl)-n-phenyl-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NC1=CC=CC=C1 NXWDZEUHBORAJK-UHFFFAOYSA-N 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 2
• OKGPJXPNOFADAQ-UHFFFAOYSA-N methyl 3-[[2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2C=3C=C(NC=3N=CC=2)C=2C3=CC(OC)=CC=C3N(C)C=2)=C1 OKGPJXPNOFADAQ-UHFFFAOYSA-N 0.000 claims description 2
• GATJDCDYZSCRKG-UHFFFAOYSA-N n-(2-methoxyethyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C1=C(OC)C=C2C(C=3NC=4N=CC=C(C=4C=3)NCCOC)=CN(C)C2=C1 GATJDCDYZSCRKG-UHFFFAOYSA-N 0.000 claims description 2
• VUISMYNHSHYGNC-UHFFFAOYSA-N n-(2-methoxyethyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=C(OC)C=C2C(C=3NC=4N=CC=C(C=4C=3)C(=O)NCCOC)=CN(C)C2=C1 VUISMYNHSHYGNC-UHFFFAOYSA-N 0.000 claims description 2
• SJIZNASJDWYKEO-UHFFFAOYSA-N n-(4-fluorophenyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NC1=CC=C(F)C=C1 SJIZNASJDWYKEO-UHFFFAOYSA-N 0.000 claims description 2
• BEJCDSFHBRRBCZ-UHFFFAOYSA-N n-(cyclopropylmethyl)-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NCC1CC1 BEJCDSFHBRRBCZ-UHFFFAOYSA-N 0.000 claims description 2
• GMQQRQJKMGSYIH-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NCC1=CC=C(F)C=C1 GMQQRQJKMGSYIH-UHFFFAOYSA-N 0.000 claims description 2
• XOVQQQXEHUBONT-UHFFFAOYSA-N n-benzyl-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C12=CC(OC)=CC=C2N(C)C=C1C(NC1=NC=C2)=CC1=C2NCC1=CC=CC=C1 XOVQQQXEHUBONT-UHFFFAOYSA-N 0.000 claims description 2
• BSEPLNALYMPGKA-UHFFFAOYSA-N n-butyl-2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-amine Chemical compound C1=C(OC)C=C2C(C=3NC=4N=CC=C(C=4C=3)NCCCC)=CN(C)C2=C1 BSEPLNALYMPGKA-UHFFFAOYSA-N 0.000 claims description 2
• UUNAXRMDUUWYDW-UHFFFAOYSA-N 2-(5-methoxy-1-methylindol-2-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylic acid Chemical compound C1=CN=C2NC(C=3N(C)C4=CC=C(C=C4C=3)OC)=CC2=C1C(O)=O UUNAXRMDUUWYDW-UHFFFAOYSA-N 0.000 claims 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• ALLKKRMIIXGTHU-UHFFFAOYSA-N methyl 2-(5-methoxy-1-methylindol-2-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxylate Chemical compound COC1=CC=C2N(C)C(C=3NC=4N=CC=C(C=4C=3)C(=O)OC)=CC2=C1 ALLKKRMIIXGTHU-UHFFFAOYSA-N 0.000 claims 1
• SUNYXEJXAYNXCL-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-2-(5-methoxy-1-methylindol-2-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound C1=CN=C2NC(C=3N(C)C4=CC=C(C=C4C=3)OC)=CC2=C1C(=O)NC(C)(C)CO SUNYXEJXAYNXCL-UHFFFAOYSA-N 0.000 claims 1
• UVRVMAUEGHOYBX-UHFFFAOYSA-N n-(2-methoxyethyl)-2-(5-methoxy-1-methylindol-2-yl)-1h-pyrrolo[2,3-b]pyridine-4-carboxamide Chemical compound COC1=CC=C2N(C)C(C=3NC=4N=CC=C(C=4C=3)C(=O)NCCOC)=CC2=C1 UVRVMAUEGHOYBX-UHFFFAOYSA-N 0.000 claims 1
• PTRHJJHEZUMSQS-UHFFFAOYSA-N n-cyclopropylpyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC1CC1 PTRHJJHEZUMSQS-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 364
• 239000007787 solid Substances 0.000 description 330
• 239000000047 product Substances 0.000 description 223
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 162
• 238000000034 method Methods 0.000 description 152
• 238000002844 melting Methods 0.000 description 127
• 230000008018 melting Effects 0.000 description 127
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 120
• 239000000243 solution Substances 0.000 description 116
• 125000000217 alkyl group Chemical group 0.000 description 114
• 239000000203 mixture Substances 0.000 description 112
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
• 229910001868 water Inorganic materials 0.000 description 81
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
• 125000003118 aryl group Chemical group 0.000 description 63
• 125000001072 heteroaryl group Chemical group 0.000 description 59
• 238000004128 high performance liquid chromatography Methods 0.000 description 59
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
• 239000011541 reaction mixture Substances 0.000 description 53
• IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 51
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 51
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 49
• 229940002612 prodrug Drugs 0.000 description 45
• 239000000651 prodrug Substances 0.000 description 45
• 238000004809 thin layer chromatography Methods 0.000 description 44
• 238000011282 treatment Methods 0.000 description 44
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
• 229910005965 SO 2 Inorganic materials 0.000 description 41
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 41
• 239000002253 acid Substances 0.000 description 38
• VAJOSPMTARTPKN-UHFFFAOYSA-N 2-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholin-4-ylethanone Chemical compound C1=C(C=2NC3=NC=CN=C3C=2)C2=CC(OC)=CC=C2N1CC(=O)N1CCOCC1 VAJOSPMTARTPKN-UHFFFAOYSA-N 0.000 description 36
• 229910052757 nitrogen Inorganic materials 0.000 description 36
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 35
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
• 239000012442 inert solvent Substances 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 32
• 238000003756 stirring Methods 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
• 239000000377 silicon dioxide Substances 0.000 description 30
• 125000004093 cyano group Chemical group *C#N 0.000 description 29
• 238000006243 chemical reaction Methods 0.000 description 27
• 125000000753 cycloalkyl group Chemical group 0.000 description 27
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 26
• 125000005843 halogen group Chemical group 0.000 description 26
• 238000010992 reflux Methods 0.000 description 23
• 229910052799 carbon Inorganic materials 0.000 description 22
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 125000003342 alkenyl group Chemical group 0.000 description 21
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 21
• 239000012634 fragment Substances 0.000 description 21
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 20
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 20
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• 125000004432 carbon atom Chemical group C* 0.000 description 20
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 20
• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 19
• 238000003818 flash chromatography Methods 0.000 description 19
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 18
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• VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
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• LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
• JLLNVEWZLBARFN-UHFFFAOYSA-N methanesulfonic acid;2-(5-methoxy-1-methylindol-3-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)OC)=CC2=C1 JLLNVEWZLBARFN-UHFFFAOYSA-N 0.000 description 1
• UAWBKMRSNQHKOA-UHFFFAOYSA-N methanesulfonic acid;2-[5-methoxy-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]-1-morpholin-4-ylethanone Chemical compound CS(O)(=O)=O.C1=C(C=2NC3=NC=CC=C3C=2)C2=CC(OC)=CC=C2N1CC(=O)N1CCOCC1 UAWBKMRSNQHKOA-UHFFFAOYSA-N 0.000 description 1
• HMSLTGXEUDAMOE-UHFFFAOYSA-N methanesulfonic acid;2-[5-methoxy-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indol-1-yl]-1-morpholin-4-ylethanone Chemical compound CS(O)(=O)=O.C1=C(C=2NC3=NC=CN=C3C=2)C2=CC(OC)=CC=C2N1CC(=O)N1CCOCC1 HMSLTGXEUDAMOE-UHFFFAOYSA-N 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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• NDBQJIBNNUJNHA-DFWYDOINSA-N methyl (2s)-2-amino-3-hydroxypropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CO NDBQJIBNNUJNHA-DFWYDOINSA-N 0.000 description 1
• MDDFRDNMAPWTEM-UHFFFAOYSA-N methyl 1-(4-methylphenyl)sulfonyl-3-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]indole-5-carboxylate Chemical compound COC(=O)C=1C=C2C(=CN(C2=CC1)S(=O)(=O)C1=CC=C(C)C=C1)C1=CC=2C(=NC=CC2)N1S(=O)(=O)C1=CC=C(C)C=C1 MDDFRDNMAPWTEM-UHFFFAOYSA-N 0.000 description 1
• OVYHABPMJWQIAZ-UHFFFAOYSA-N methyl 1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carboxylate Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)C(=O)OC)=CC2=N1 OVYHABPMJWQIAZ-UHFFFAOYSA-N 0.000 description 1
• WVGUVNOCMJAHQR-UHFFFAOYSA-N methyl 1-methyl-3-[1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]indole-6-carboxylate Chemical compound C=1N(C)C2=CC(C(=O)OC)=CC=C2C=1C1=CC2=CC=CN=C2N1S(=O)(=O)C1=CC=C(C)C=C1 WVGUVNOCMJAHQR-UHFFFAOYSA-N 0.000 description 1
• AYYOZKHMSABVRP-UHFFFAOYSA-N methyl 1h-indole-6-carboxylate Chemical compound COC(=O)C1=CC=C2C=CNC2=C1 AYYOZKHMSABVRP-UHFFFAOYSA-N 0.000 description 1
• KXSYSWDIVYLYGF-UHFFFAOYSA-N methyl 2-[6-(4-tert-butylphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2-methyl-3-oxobutanoate Chemical compound COC(=O)C(C)(C(C)=O)c1c([nH]c2nccnc12)-c1ccc(cc1)C(C)(C)C KXSYSWDIVYLYGF-UHFFFAOYSA-N 0.000 description 1
• KCBDEKXPSQVLEP-UHFFFAOYSA-N methyl 2-[[2-[5-methoxy-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]acetyl]amino]-3-methylpentanoate Chemical compound C12=CC(OC)=CC=C2N(CC(=O)NC(C(C)CC)C(=O)OC)C=C1C1=CC2=CC=CN=C2N1 KCBDEKXPSQVLEP-UHFFFAOYSA-N 0.000 description 1
• YPPMOQSQWQHRMK-UHFFFAOYSA-N methyl 3-(4-chloro-1h-pyrrolo[2,3-b]pyridin-2-yl)-1-methylindole-5-carboxylate Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)C(=O)OC)=CC2=C1Cl YPPMOQSQWQHRMK-UHFFFAOYSA-N 0.000 description 1
• FGOZFBAWDDMQHB-UHFFFAOYSA-N methyl 3-(4-cyano-1h-pyrrolo[2,3-b]pyridin-2-yl)-1-methylindole-5-carboxylate Chemical compound C1=CN=C2NC(C3=CN(C)C4=CC=C(C=C43)C(=O)OC)=CC2=C1C#N FGOZFBAWDDMQHB-UHFFFAOYSA-N 0.000 description 1
• XOAQNGALOTYKLS-UHFFFAOYSA-N methyl 3-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]-1-methylindole-5-carboxylate Chemical compound COC(=O)C=1C=C2C(=CN(C2=CC1)C)C1=CC=2C(=NC=CC2C=2C(=NOC2C)C)N1S(=O)(=O)C1=CC=C(C)C=C1 XOAQNGALOTYKLS-UHFFFAOYSA-N 0.000 description 1
• IBFFABAKDBOXTA-UHFFFAOYSA-N methyl 3-[4-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]-1H-indole-5-carboxylate Chemical compound COC(=O)C=1C=C2C(=CNC2=CC1)C1=CC=2C(=NC=CC2C=2C(=NOC2C)C)N1S(=O)(=O)C1=CC=C(C)C=C1 IBFFABAKDBOXTA-UHFFFAOYSA-N 0.000 description 1
• LNXUMJPAJXRUDJ-UHFFFAOYSA-N methyl 3-[4-chloro-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]-1-methylindole-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2N(C)C=C1C1=CC2=C(Cl)C=CN=C2N1S(=O)(=O)C1=CC=C(C)C=C1 LNXUMJPAJXRUDJ-UHFFFAOYSA-N 0.000 description 1
• GXUYEOPXCZLGDB-UHFFFAOYSA-N methyl 3-[4-methoxy-1-(4-methylphenyl)sulfonylpyrrolo[2,3-b]pyridin-2-yl]-1-methylindole-5-carboxylate Chemical compound COC(=O)C=1C=C2C(=CN(C2=CC1)C)C1=CC=2C(=NC=CC2OC)N1S(=O)(=O)C1=CC=C(C)C=C1 GXUYEOPXCZLGDB-UHFFFAOYSA-N 0.000 description 1
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• RIYDZDVMOLPOSA-UHFFFAOYSA-N n-(1,3-dihydroxy-2-methylpropan-2-yl)-1-methyl-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indole-5-carboxamide Chemical compound C12=CC(C(=O)NC(C)(CO)CO)=CC=C2N(C)C=C1C1=CC2=CC=CN=C2N1 RIYDZDVMOLPOSA-UHFFFAOYSA-N 0.000 description 1
• NUWVHJZFJTVFFF-UHFFFAOYSA-N n-(1-adamantyl)-2-[5-methoxy-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]acetamide Chemical compound C1=CN=C2NC(C3=CN(CC(=O)NC45CC6CC(CC(C6)C4)C5)C4=CC=C(C=C43)OC)=CC2=C1 NUWVHJZFJTVFFF-UHFFFAOYSA-N 0.000 description 1
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• APTYWMXFUGYVGM-UHFFFAOYSA-N n-(1-cyclohexylethyl)-2-[5-methoxy-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]acetamide Chemical compound C1=C(C=2NC3=NC=CC=C3C=2)C2=CC(OC)=CC=C2N1CC(=O)NC(C)C1CCCCC1 APTYWMXFUGYVGM-UHFFFAOYSA-N 0.000 description 1
• ZZNPIMREDONCNL-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carboxamide Chemical compound C12=CC(C(=O)NC(C)(C)CO)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 ZZNPIMREDONCNL-UHFFFAOYSA-N 0.000 description 1
• QLWVZFKXLGZRBW-UHFFFAOYSA-N n-(1-hydroxy-2-methylpropan-2-yl)-1-methyl-3-(5h-pyrrolo[2,3-b]pyrazin-6-yl)indole-5-carboxamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.C12=CC(C(=O)NC(C)(C)CO)=CC=C2N(C)C=C1C1=CC2=NC=CN=C2N1 QLWVZFKXLGZRBW-UHFFFAOYSA-N 0.000 description 1
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• KLUNYVGERQVDEL-UHFFFAOYSA-N n-(1-hydroxy-3-methylpentan-2-yl)-2-[5-methoxy-3-(1h-pyrrolo[2,3-b]pyridin-2-yl)indol-1-yl]acetamide Chemical compound C12=CC(OC)=CC=C2N(CC(=O)NC(CO)C(C)CC)C=C1C1=CC2=CC=CN=C2N1 KLUNYVGERQVDEL-UHFFFAOYSA-N 0.000 description 1
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