2-(2,4-Difluorophenyl)-1,3-thiazole-4-carboxylic acid → HCID 86713953, compound

HRID 522061Notes

Reaction equation

HRID 522061 reaction equation
[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]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[C:34]1[S:35][CH:36]=[C:37]([C:39](O)=[O:40])[N:38]=1>>[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:39]([C:37]2[N:38]=[C:34]([C:28]3[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=3[F:26])[S:35][CH:36]=2)=[O:40])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 183514782-(2,4-Difluorophenyl)-1,3-thiazole-4-carboxylic acidHCID 86713841tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate2×

Product 1

HCID 86713953HCID 86713953, compound

Procedure

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 2-(2,4-difluorophenyl)thiazole-4-carboxylic acid (see US2008/76771) gave 325. 1H NMR (400 MHz, DMSO-d6) δ 9.89 (s, 1H), 8.56-8.46 (m, 2H), 7.88 (s, 1H), 7.59-7.50 (m, 1H), 7.32-7.24 (m, 1H), 4.87 (dd, J=10.4, 3.5 Hz, 1H), 4.57-4.38 (m, 1H), 4.38-4.23 (m, 1H), 4.18-3.98 (m, 1H), 3.78 (s, 3H), 2.14-2.02 (m, 1H), 1.88-1.66 (m, 4H). LCMS (ES+) m/z 452 (M+1).

Sources & evidence

ORD record
ord-e9166d34850d4f85b5ac189b9968c9ad
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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