5-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid → HCID 74983238, compound

HRID 1915933Notes

Reaction equation

HRID 1915933 reaction equation
[CH3:1][N:2]1[C:6]([N:7]2[CH2:13][CH2:12][CH2:11][C:10]([C:15]([F:18])([F:17])[F:16])([OH:14])[CH2:9][CH2:8]2)=[C:5]([N+:19]([O-])=O)[CH:4]=[N:3]1.C(OC([NH:29][C:30]1[S:34][C:33]([C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])=[N:32][C:31]=1[C:43](O)=[O:44])=O)(C)(C)C>>[NH2:29][C:30]1[S:34][C:33]([C:35]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:36]=2[F:42])=[N:32][C:31]=1[C:43]([NH:19][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[N:7]1[CH2:13][CH2:12][CH2:11][C:10]([OH:14])([C:15]([F:18])([F:17])[F:16])[CH2:9][CH2:8]1)=[O:44]

Participants

3

Reactant 2

HCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acidHCID 86680134HCID 86680134, compound

Product 1

HCID 74983238HCID 74983238, compoundYield 29%

Procedure

Following the procedure for Example 101 starting from 1-(1-methyl-4-nitro-1H-pyrazol-5-yl)-4-(trifluoromethyl)azepan-4-ol and 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)-thiazole-4-carboxylic acid gave 405 as a pale brown solid (53 mg, 29% over three steps). 1H NMR (400 MHz, CDCl3) δ 8.95 (s, 1H), 7.94 (s, 1H), 7.39-7.28 (m, 1H), 7.02 (t, J=8.7 Hz, 2H), 6.21 (s, 2H), 3.73 (s, 3H), 3.46 (ddd, J=13.7, 8.5, 5.0 Hz, 1H), 3.29-3.18 (m, 3H), 2.95 (s, 1H), 2.15-1.97 (m, 5H), 1.87-1.77 (m, 1H). LCMS (ES+) m/z 517 (M+1)

Sources & evidence

ORD record
ord-cb0b5bffe48d4637a91da8cd3bf8fff4
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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