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

HRID 2363084Notes

Reaction equation

HRID 2363084 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].[CH2:25]([N:27]([CH2:35][CH3:36])[C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1)[CH3:26]>>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21]([O:34][C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([N:27]([CH2:35][CH3:36])[CH2:25][CH3:26])[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 70623-(Diethylamino)phenolHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 671111822-(3-Diethylamino-phenoxy)-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amideYield 39.3%

Procedure

2-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (50 mg, 0.13 mmol) was reacted with 3-diethylamino phenol (44 mg, 0.26 mmol) to give the title compound (26 mg, 39%) after purification by column chromatography (gradient 12% to 100% EtOAc in n-hexane).

Sources & evidence

ORD record
ord-9ab4be87f135483095757bf761284173
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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