Triethylamine → HCID 178457501, compound

Participants

Reaction Steps

Trans-3-(4-aminocyclohexylcarbonylamino)-5-dimethylaminocarbonyl-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide hydrochloride (160 mg) obtained in Example 344 is suspended in dichloromethane (8 ml), and thereto are added successively triethylamine (129 μl), acetone (113 μl), and sodium triacetoxy borohydride (130 mg) under ice-cooling, and the reaction solution is warmed to room temperature, and stirred for 17 hours. Under ice-cooling, to the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is washed with a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate, then chloroform/methanol=30/1). The resulting residue is dissolved in ethanol, and thereto is added 4N hydrogen chloride in ethyl acetate. The reaction solution is concentrated and the resulting residue is suspended in diethyl ether. The precipitates are collected by filtration to give the title compound (94 mg).

Provenance & Evidence