Reacción #72108

Ecuación de reacción

4-Chloro-5-ethyl-1H-imidazole-2-carboxylic acid

1-hydroxybenzotriazole

1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride

triethylamine

Ethyl cis-3-(4-aminocyclohexyl)benzoate

→

title compound

Rendimiento 53.8%

Ethyl cis-3-{4-[(4-chloro-5-ethyl-1H-imidazole-2-carbonyl)amino]cyclohexyl}benzoate

Rendimiento 53.8%

Disolventes

ethyl acetate

N,N-dimethylacetamide dichloromethane

1/1

water TFA

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with brine
2. 2
   Secadodried over magnesium sulfate
3. 3
   OtroThe solvent was evaporated under reduced pressure
4. 4
   OtroThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1)

Procedimiento

Ethyl cis-3-(4-aminocyclohexyl)benzoate obtained in Example (194a) (57 mg, 0.23 mmol) was dissolved in a mixed solution of N,N-dimethylacetamide/dichloromethane=1/1 (10 mL). 4-Chloro-5-ethyl-1H-imidazole-2-carboxylic acid (described in Example 1d, 60 mg, 0.345 mmol), 1-hydroxybenzotriazole (64 mg, 0.472 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (90 mg, 0.472 mmol) and triethylamine (66 μL, 0.472 mmol) were added, and the mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, washed with brine, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1) to obtain 50 mg of the title compound as a white solid (53%).

Fuente