تفاعل #72108

معادلة التفاعل

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

المردود 53.8%

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

المردود 53.8%

المذيبات

ethyl acetate

N,N-dimethylacetamide dichloromethane

1/1

water TFA

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر