HCID 70655806, compound → HCID 86713889, compound

HRID 521975Notes

Reaction equation

HRID 521975 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]=[C:31]([C:33]2([OH:39])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH:30]=[C:29]([F:40])[C:28]=1[C:41]1[N:46]=[C:45]([C:47](O)=[O:48])[CH:44]=[CH:43][C:42]=1[F:50]>>[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:47](=[O:48])[C:45]2[CH:44]=[CH:43][C:42]([F:50])=[C:41]([C:28]3[C:29]([F:40])=[CH:30][C:31]([C:33]4([OH:39])[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)=[CH:32][C:27]=3[F:26])[N:46]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 70655806HCID 70655806, compoundHCID 86713841tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate2×

Product 1

HCID 86713889HCID 86713889, 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 6-(2,6-difluoro-4-(4-hydroxytetrahydro-2H-pyran-4-yl)phenyl)-5-fluoropicolinic acid (see US2012/225062) gave 196. 1H NMR (400 MHz, DMSO-d6) δ 10.19 (s, 1H), 8.29 (dd, J=8.7, 4.0 Hz, 1H), 8.23-8.10 (m, 1H), 7.88 (s, 1H), 7.49-7.35 (m, 2H), 4.85-4.76 (m, 1H), 4.39-4.11 (m, 1H), 4.07-3.68 (m, 9H), 3.17-3.03 (m, 1H), 2.11-1.99 (m, 3H), 1.84-1.51 (m, 5H). LCMS (ES+) m/z 564 (M+1).

Sources & evidence

ORD record
ord-d262035fdcd3459697033f3e62aba8af
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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