4'-Trifluoromethylbiphenyl-2-carboxylic acid (4-benzyloxy-2-dimethylcarbamoylphenyl)amide → 4'-Trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-hydroxyphenyl)amide

HRID 2114179Notes

Reaction equation

HRID 2114179 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:19]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:17])=[C:11]([C:34](=[O:38])[N:35]([CH3:37])[CH3:36])[CH:10]=1)C1C=CC=CC=1>CO.C1COCC1.[C].[Pd]>[CH3:36][N:35]([CH3:37])[C:34]([C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[NH:15][C:16]([C:18]1[C:19]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=2)=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:17])=[O:38]

Participants

5

Reactant 1

HCID 587064144'-Trifluoromethylbiphenyl-2-carboxylic acid (4-benzyloxy-2-dimethylcarbamoylphenyl)amide

Product 1

HCID 587063754'-Trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-hydroxyphenyl)amideYield 105.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4′-Trifluoromethylbiphenyl-2-carboxylic acid (4-benzyloxy-2-dimethylcarbamoylphenyl)amide (1.2 g) was dissolved in MeOH (25 mL)-THF (25 mL), and thereto was added 7.5% palladium carbon (250 mg). The mixture was stirred for 5 hours under hydrogen atmosphere. The reaction solution was filtered through a Celite and the filtrate was concentrated to give 4′-trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-hydroxyphenyl)amide (1.05 g).

Workup

  1. filtrationThe reaction solution was filtered through a Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7dae8e8a460c46859b31e04a7b1366a0
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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