6-(2,6-Difluorophenyl)-5-fluoropicolinic acid → N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-6-(2,6-difluorophenyl)-5-fluoropicolinamide

HRID 521974

반응식

HRID 521974 반응식
[F:1][C@H:2]1[C@H:8]([NH:9]C(=O)OC(C)(C)C)[CH2:7][CH2:6][C@@H:5]([C:17]2[N:21]([CH3:22])[N:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[O:4][CH2:3]1.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=1[C:34]1[N:39]=[C:38]([C:40](O)=[O:41])[CH:37]=[CH:36][C:35]=1[F:43]>>[NH2:9][C@H:8]1[C@H:2]([F:1])[CH2:3][O:4][C@H:5]([C:17]2[N:21]([CH3:22])[N:20]=[CH:19][C:18]=2[NH:23][C:40](=[O:41])[C:38]2[CH:37]=[CH:36][C:35]([F:43])=[C:34]([C:28]3[C:27]([F:26])=[CH:32][CH:31]=[CH:30][C:29]=3[F:33])[N:39]=2)[CH2:6][CH2:7]1

참가 물질

3

반응물 2

HCID 592265526-(2,6-Difluorophenyl)-5-fluoropicolinic acidHCID 86713841tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate2회

생성물 1

HCID 73437699N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-6-(2,6-difluorophenyl)-5-fluoropicolinamide

실험 절차

Following the procedure for Example 111 starting from tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate (Intermediate 80), and replacing 5-((tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid with 6-(2,6-difluorophenyl)-5-fluoropicolinic acid (see US2012/225061) gave 195. 1H NMR (400 MHz, DMSO-d6) δ 10.20 (s, 1H), 8.30 (dd, J=8.7, 4.0 Hz, 1H), 8.15 (t, J=8.9 Hz, 1H), 7.91 (s, 1H), 7.72-7.59 (m, 1H), 7.30 (t, J=8.4 Hz, 2H), 4.86-4.78 (m, 1H), 4.31-4.05 (m, 1H), 4.02-3.83 (m, 2H), 3.75 (s, 3H), 3.11-2.97 (m, 1H), 2.11-2.00 (m, 1H), 1.82-1.50 (m, 5H). LCMS (ES+) m/z 464 (M+1).

출처 및 근거

ORD 기록
ord-72b29aa318e145198198cdfcb13d06bb
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328106B2

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