HCID 43140181, compound → HCID 86713942, compound

HRID 522051Notes

Reaction equation

HRID 522051 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]([F:43])([F:42])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=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:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[C:27]([F:43])([F:26])[F:42])[S:35][CH:36]=2)=[O:40])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 43140181HCID 43140181, compound2×HCID 86713841tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate2×

Product 1

HCID 86713942HCID 86713942, 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-(trifluoromethyl)phenyl)thiazole-4-carboxylic acid (Intermediate 124) gave 311. 1H NMR (400 MHz, DMSO-d6) δ 9.75 (s, 1H), 8.58 (s, 1H), 7.97-7.93 (m, 1H), 7.89-7.75 (m, 4H), 4.78 (dd, J=10.9, 3.7 Hz, 1H), 4.37-4.19 (m, 1H), 4.14-4.02 (m, 1H), 4.02-3.84 (m, 1H), 3.78 (s, 3H), 3.20-3.08 (m, 1H), 2.08-1.99 (m, 1H), 1.88-1.76 (m, 1H), 1.71-1.59 (m, 3H). LCMS (ES+) m/z 484 (M+1).

Sources & evidence

ORD record
ord-e150b530f3da42449975a915cec7499f
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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