1,1'-Carbonyldiimidazole → Imidazole-1-carboxylic acid [5-(2-tert-butyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-amide

HRID 2370360Notes

Reaction equation

HRID 2370360 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[S:15][C:14]([NH2:16])=[N:13][C:12]=2[CH3:17])[CH:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:18](N1C=CN=C1)([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19]>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[S:15][C:14]([NH:16][C:18]([N:20]3[CH:24]=[CH:23][N:22]=[CH:21]3)=[O:19])=[N:13][C:12]=2[CH3:17])[CH:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 574170735-(2-Tert-butylpyridin-4-yl)-4-methylthiazol-2-amine

Product 1

HCID 59293666Imidazole-1-carboxylic acid [5-(2-tert-butyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-amideYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(2-tert-butyl-pyridin-4-yl)-4-methyl-thiazol-2-ylamine (Step 1.2) (1 g, 4.05 mmol) and 1,1′-carbonyldiimidazole (0.984 g, 6.07 mmol, 1.5 eq) in DCM (50 mL) is stirred for 4 h at reflux and allowed to cool. The resulting precipitate is collected by filtration to provide 1.26 g of the title compound as white solid: ESI-MS: 340.2 [M−H]−; tR=2.85 min (System 1).

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. filtrationThe resulting precipitate is collected by filtration

Sources & evidence

ORD record
ord-94a6106c4499482dbdc36f4210e750d6
Source dataset
uspto-grants-2014_04
Patent number
US08710085B2

Reaction notes

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