Imidazole → Acetamide, N-[5-[3-(1H-imidazol-1-YL)-4-(methylsulfonyl)phenyl]-4-methyl-2-thiazolyl]-

HRID 1092977Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][C:13]=2[CH3:21])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[N:22]1([C:2]2[CH:3]=[C:4]([C:12]3[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][C:13]=3[CH3:21])[CH:5]=[CH:6][C:7]=2[S:8]([CH3:11])(=[O:10])=[O:9])[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

Conditions

Temperature: 140 °C

Procedure

A stirred mixture of N-[5-(3-Fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 64) (0.1 g, 0.30 mmol), imidazole (0.069 g, 0.90 mmol) and caesium carbonate (0.198 g, 0.60 mmol) in dry DMSO is heated under argon at 140° C. for 2 hours. The solvent is removed and water (30 ml) is added. The product is extracted with ethyl acetate (2×30 ml) and the combined organic extracts are washed with brine (20 ml) and dried (MgSO4). Removal of the solvent and trituration with methanol affords the titled compound as an orange solid. 377.9721

Workup

customThe solvent is removed
additionwater (30 ml) is added
extractionThe product is extracted with ethyl acetate (2×30 ml)
washthe combined organic extracts are washed with brine (20 ml)
dry with materialdried (MgSO4)
customRemoval of the solvent and trituration with methanol

Sources & evidence

ORD record: ord-7aa0cf6e25bb4d25a1e6e6bea46ffd03
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129541B2

Reaction notes

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