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

HRID 2363082Notes

Reaction equation

HRID 2363082 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:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=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:30]3[CH:31]=[CH:32][C:27]([C:26]([F:25])([F:34])[F:35])=[CH:28][CH:29]=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 678744-(Trifluoromethyl)phenolHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 672384702-(4-Trifluoromethyl-phenoxy)-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amideYield 68.5%

Procedure

2-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (50 mg, 0.13 mmol) was reacted with 4-trifluoromethyl phenol (43 mg, 0.26 mmol) to give the title compound (45 mg, 67%) after purification by column chromatography (gradient 12% to 100% EtOAc in n-hexane).

Sources & evidence

ORD record
ord-f4438c6b8d81445ca58f25206c7989a8
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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