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

HRID 1430145Notes

Reaction equation

HRID 1430145 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:17])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2([CH3:16])[CH2:15][CH2:14]2)[CH:8]=1.[C:18](N1C=CN=C1)([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19]>C(Cl)Cl>[CH3:1][C:2]1[N:3]=[C:4]([NH:17][C:18]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[O:19])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2([CH3:16])[CH2:15][CH2:14]2)[CH:8]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 575066604-Methyl-5-(2-(1-methylcyclopropyl)pyridin-4-yl)thiazol-2-amine

Product 1

HCID 86631916Imidazole-1-carboxylic acid {4-methyl-5-[2-(1-methyl-cyclopropyl)-pyridin-4-yl]-thiazol-2-yl}amideYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-methyl-5-[2-(1-methyl-cyclopropyl)-pyridin-4-yl]-thiazol-2-ylamine (Step 40.2) (211 mg, 0.86 mmol) and 1,1′-carbonyldiimidazole (210 mg, 1.3 mmol, 1.5 eq) in DCM (10 mL) is stirred for 14 h at reflux and allowed to cool. The resulting precipitate is collected by filtration to provide 275 mg of the title compound as white solid: ESI-MS: 338.2 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-a3ffd0317e3946ecb94695d4fcb265a5
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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