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

HRID 1092986
Notes
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Reaction equation

HRID 1092986 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 574737535-(3-Imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine

Product 1

HCID 86598422Imidazole-1-carboxylic acid [5-(3-imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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

  1. temperatureThe reaction mixture is cooled
  2. filtrationthe resulting solid filtered
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes