HCID 73437926, compound → HCID 73438360, compound

HRID 521986Notes

Reaction equation

HRID 521986 reaction equation
F[C@H]1[C@H](NC(=O)OC(C)(C)C)CC[C@@H:5]([C:17]2N(C)N=[CH:19][C:18]=2[N+]([O-])=O)[O:4]C1.N[C:27]1[S:31][C:30]([C:32]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:33]=2[F:39])=[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[C:33]([F:39])=[CH:34][C:35]([CH:18]4[CH2:17][CH2:5][O:4][CH2:19]4)=[CH:36][C:37]=3[F:38])[S:31][CH:27]=2)=[O:41])[CH2:54][CH2:53]1

Participants

3

Reactant 2

HCID 73437926HCID 73437926, 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 73438360HCID 73438360, 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-(2,6-difluoro-4-(tetrahydrofuran-3-yl)phenyl)thiazole-4-carboxylic acid (Intermediate 145) gave 216. The product was isolated as a mixture of diastereomers. 1H NMR (400 MHz, DMSO-d6) δ 9.85 (s, 1H), 8.61 (s, 1H), 7.80 (s, 1H), 7.27 (d, J=10.0 Hz, 2H), 4.81 (dd, J=10.8, 3.7 Hz, 1H), 4.46-4.22 (m, 1H), 4.24-4.09 (m, 1H), 4.08-3.89 (m, 3H), 3.86-3.75 (m, 4H), 3.63 (dd, J=8.4, 6.9 Hz, 1H), 3.58-3.45 (m, 1H), 3.34-3.16 (m, 3H), 2.42-2.29 (m, 1H), 2.11-1.91 (m, 2H), 1.87-1.79 (m, 1H), 1.72-1.62 (m, 4H). LCMS (ES+) m/z 522 (M+1).

Sources & evidence

ORD record
ord-1451ab6e9fbd4927afe172bfc352c630
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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