2-(2-Fluorophenyl)-1,3-thiazole-4-carboxylic acid → HCID 86713946, compound

HRID 522054Notes

Reaction equation

HRID 522054 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 86713831tert-butyl ((3R,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate2×

Product 1

HCID 86713946HCID 86713946, compound

Procedure

Following the procedure for Example 111 starting from tert-butyl ((3R,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate (Intermediate 24), 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 318. 1H NMR (400 MHz, DMSO-d6) δ 10.08 (s, 1H), 8.53 (s, 1H), 8.35-8.28 (m, 1H), 7.81 (s, 1H), 7.66-7.58 (m, 1H), 7.53-7.41 (m, 2H), 5.02-4.81 (m, 2H), 4.24-4.09 (m, 1H), 4.09-3.92 (m, 1H), 3.77 (s, 3H), 2.20-2.09 (m, 1H), 2.07-1.92 (m, 1H), 1.87-1.74 (m, 2H), 1.66 (d, J=13.1 Hz, 1H). LCMS (ES+) m/z 434 (M+1).

Sources & evidence

ORD record
ord-0a82e0b56dbb4b90b6583387fad82363
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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