反応 #72025

反応方程式

sodium bicarbonate

cis(±)-4-chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride

→

cis(±)-4-{[(5-chloro-4-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidine

溶媒

Ethyl acetate

反応条件

後処理

1. 1
   抽出the aqueous layer was extracted with ethyl acetate
2. 2
   乾燥Thereafter, drying over anhydrous sodium sulfate

実験手順

Ethyl acetate and saturated sodium bicarbonate solution were added to cis(±)-4-chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (0.100 g, 0.296 mmol), and the aqueous layer was extracted with ethyl acetate. Thereafter, drying over anhydrous sodium sulfate gave cis(±)-4-{[(5-chloro-4-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidine. This and 3-{(S)-2-methoxycarbonylpyrrolidine-1-carbonyl}-3-methyl-1H-imidazol-3-ium iodide obtained in Example (151b) (0.162 g, 0.444 mmol) were dissolved in dichloromethane (5 ml), and the solution was stirred at room temperature for 24 hours. Water and ethyl acetate were added to the reaction solution, followed by extraction with ethyl acetate and further extraction with dichloromethane. The organic layers were combined and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=1/1, then methanol/ethyl acetate=0/100, 5/95, 10/90) to obtain 38 mg of the crude title compound. This was further purified by thin layer silica gel chromatography (developing solvent: methanol/dichloromethane=5/95) to obtain 24 mg of the title compound as a colorless oily substance (18%).

出典