HCID 58465104, compound → HCID 86713948, compound

HRID 522056Notes

Reaction equation

HRID 522056 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.C(OC([NH:33][C:34]1[S:38][C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:36][C:35]=1[C:45](O)=[O:46])=O)(C)(C)C>>[NH2:33][C:34]1[S:38][C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:36][C:35]=1[C:45]([NH:23][C:18]1[CH:19]=[N:20][N:21]([CH3:22])[C:17]=1[C@@H:5]1[CH2:6][CH2:7][C@@H:8]([NH2:9])[C@H:2]([F:1])[CH2:3][O:4]1)=[O:46]

Participants

3

Reactant 2

HCID 58465104HCID 58465104, compoundHCID 86713841tert-butyl ((3S,4R,7S)-3-fluoro-7-(1-methyl-4-nitro-1H-pyrazol-5-yl)oxepan-4-yl)carbamate2×

Product 1

HCID 86713948HCID 86713948, 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 5-((tert-butoxycarbonyl)amino)-2-phenylthiazole-4-carboxylic acid (Example 6) gave 320. 1H NMR (400 MHz, DMSO-d6) δ 9.29 (s, 1H), 7.89-7.81 (m, 2H), 7.50-7.34 (m, 4H), 7.01-6.59 (m, 1H), 4.83 (dd, J=10.7, 3.5 Hz, 1H), 4.57-4.39 (m, 1H), 4.37-3.99 (m, 2H), 3.80-3.70 (m, 3H), 2.04 (d, J=13.7 Hz, 1H), 2.00-1.66 (m, 4H). LCMS (ES+) m/z 431 (M+1).

Sources & evidence

ORD record
ord-e3683d5048544873af466401896d80b5
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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