3-(Trifluoromethyl)phenol → 2-(3-Trifluoromethyl-phenoxy)-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

HRID 2363078Notes

Reaction equation

HRID 2363078 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21](Cl)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[F:25][C:26]([F:35])([F:34])[C:27]1[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21]([O:33][C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([F:25])([F:34])[F:35])[CH:28]=3)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 73763-(Trifluoromethyl)phenolHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 446029362-(3-Trifluoromethyl-phenoxy)-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amideYield 82%

Procedure

2-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (40 mg, 0.11 mmol) was reacted with 3-trifluoromethyl phenol (20 mg, 0.12 mmol) to give the title compound (42 mg, 82%) after purification by column chromatography (gradient 12% to 100% EtOAc in n-hexane).

Sources & evidence

ORD record
ord-f60fb7aa817f4c63855c7135d65de0ca
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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