tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate → HCID 73438409, compound

HRID 522050Notes

Reaction equation

HRID 522050 reaction equation
[F:1][C@H]1[C@H](NC(=O)OC(C)(C)C)CC[C@@H](C2N(C)N=CC=2[N+]([O-])=O)OC1.N[C:27]1[S:31][C:30]([C:32]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=2F)=[N:29][C:28]=1[C:40]([NH:42][C:43]1[CH:44]=[N:45][N:46]([CH3:57])[C:47]=1[CH:48]1[CH2:54][CH2:53][C@@H:52]([NH2:55])[C@@H:51]([F:56])[CH2:50][O:49]1)=[O:41]>>[NH2:55][C@H:52]1[C@H:51]([F:56])[CH2:50][O:49][C@H:48]([C:47]2[N:46]([CH3:57])[N:45]=[CH:44][C:43]=2[NH:42][C:40]([C:28]2[N:29]=[C:30]([C:32]3[CH:33]=[CH:34][CH:35]=[C:36]([F:1])[C:37]=3[F:38])[S:31][CH:27]=2)=[O:41])[CH2:54][CH2:53]1

Participants

3

Reactant 2

HCID 86713841tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate2×HCID 86713941HCID 86713941, compound2×

Product 1

HCID 73438409HCID 73438409, 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-(2,3-difluorophenyl)thiazole-4-carboxylic acid (Intermediate 119) gave 306. 1H NMR (400 MHz, DMSO-d6) δ 9.90 (s, 1H), 8.59 (s, 1H), 8.28-8.21 (m, 1H), 7.87 (s, 1H), 7.68-7.58 (m, 1H), 7.44-7.36 (m, 1H), 4.88 (dd, J=10.5, 3.5 Hz, 1H), 4.67-4.49 (m, 1H), 4.41-4.29 (m, 1H), 4.20-4.03 (m, 2H), 3.79 (s, 3H), 3.45-3.35 (m, 1H), 2.15-2.05 (m, 1H), 1.91-1.73 (m, 3H). LCMS (ES+) m/z 452 (M+1).

Sources & evidence

ORD record
ord-4caa6f72b65447a895d43322e49ca7cb
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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