Sodium hydride → Imidazole-1-carboxylic acid [5-(3-imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide

HRID 1092986Notes

Reaction equation

[H-].[Na+].[N:3]1([C:8]2[CH:9]=[C:10]([C:18]3[S:22][C:21]([NH2:23])=[N:20][C:19]=3[CH3:24])[CH:11]=[CH:12][C:13]=2[S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:6][N:5]=[CH:4]1.[C:25](N1C=CN=C1)([N:27]1[CH:31]=[CH:30][N:29]=[CH:28]1)=[O:26]>CN(C)C=O>[N:3]1([C:8]2[CH:9]=[C:10]([C:18]3[S:22][C:21]([NH:23][C:25]([N:27]4[CH:31]=[CH:30][N:29]=[CH:28]4)=[O:26])=[N:20][C:19]=3[CH3:24])[CH:11]=[CH:12][C:13]=2[S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

Conditions

Temperature: 40 °C

Procedure

Sodium hydride (60% dispersion in oil, 0.137 g, 3.42 mmol) is added to a stirred suspension of 5-(3-Imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (148) (1.04 g, 3.1 mmol) in dry dimethylformamide (10 ml) at room temperature under argon. 1,1′-Carbonyl diimidazole (0.757 g, 4.67 mmol) is added and the stirred suspension is heated to 40° C. for 1 h. The reaction mixture is cooled and the resulting solid filtered and washed with DCM and ether to afford the title compound.

Workup

temperatureThe reaction mixture is cooled
filtrationthe resulting solid filtered
washwashed with DCM and ether

Sources & evidence

ORD record: ord-cccd21f78e3048059dd019d822418b01
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129541B2

Reaction notes

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