2-(2-Fluorophenyl)-1,3-thiazole-4-carboxylic acid → HCID 86713950, compound

HRID 522058Notes

Reaction equation

HRID 522058 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]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]1[S:34][CH:35]=[C:36]([C:38](O)=[O:39])[N:37]=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:38]([C:36]2[N:37]=[C:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[F:26])[S:34][CH:35]=2)=[O:39])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 431423062-(2-Fluorophenyl)-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 86713950HCID 86713950, 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-fluorophenyl)thiazole-4-carboxylic acid (see Bioorg. Med. Chem. Lett. 2010, 20, 1758) gave 322. 1H NMR (400 MHz, DMSO-d6) δ 9.90 (s, 1H), 8.53 (s, 1H), 8.52-8.44 (m, 1H), 7.89 (s, 1H), 7.63-7.56 (m, 1H), 7.51-7.37 (m, 2H), 4.88 (dd, J=10.6, 3.6 Hz, 1H), 4.57-4.39 (m, 1H), 4.38-4.25 (m, 1H), 4.20-3.99 (m, 1H), 3.79 (s, 3H), 2.13-2.05 (m, 1H), 1.90-1.78 (m, 1H), 1.75 (d, J=9.6 Hz, 3H). LCMS (ES+) m/z 434 (M+1).

Sources & evidence

ORD record
ord-0a1fca1718424ac4a77755d6a8b63ae8
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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