2-Benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-(2 methylthiazol-4-yl)benzamide → N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-(2-methylthiazol-4-yl)benzamide

HRID 644413Notes

Reaction equation

HRID 644413 reaction equation
C([O:8][C:9]1[CH:31]=[CH:30][C:29]([C:32]2[N:33]=[C:34]([CH3:37])[S:35][CH:36]=2)=[CH:28][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)=[O:12])C1C=CC=CC=1>C(O)C.[Pd]>[F:27][C:24]([F:25])([F:26])[C:16]1[CH:15]=[C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:28]=[C:29]([C:32]3[N:33]=[C:34]([CH3:37])[S:35][CH:36]=3)[CH:30]=[CH:31][C:9]=2[OH:8])[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=1

Participants

4

Reactant 1

HCID 178602912-Benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-(2 methylthiazol-4-yl)benzamide

Product 1

HCID 10095074N-[3,5-Bis(trifluoromethyl)phenyl]-2-hydroxy-5-(2-methylthiazol-4-yl)benzamideYield 79.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-(2-methylthiazol-4-yl)benzamide (160 mg, 0.3 mmol) and 10% Pd—C (240 mg) were dissolved in ethanol (10 ml) and stirred for 3.5 hours under hydrogen atmosphere. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure to give the title compound (103.4 mg, 79.2%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-12ffdc3932cb41798b4df66cea79e840
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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