Diisopropylethylamine → HCID 178512337, compound

Participants

Reaction Steps

Diisopropylethylamine (107 uL, 0.615 mmol) was added to a solution of (3R) 3-amino-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (205 mg, 0.615 mmol) and diphenyl N-cyanocarbonimidate (147 mg, 0.615 mmol) in methylene chloride (5 mL). The reaction was stirred at room temperature for 72 h, then quenched with 0.5 N sodium hydroxide. The methylene chloride was washed with water and saturated brine, and dried over sodium sulfate. The solid product (139 mg, 0.291 mmol) was dissolved in 1-pentanol (2 mL) along with 4-phenyl-1-piperidin-4-yl-1,3-dihydro-2H-imidazol-2-one hydrochloride (81.4 mg, 0.291 mmol) and diisopropylethylamine (76.1 uL, 0.437 mmol), and refluxed under argon overnight. An additional equivalent of 4-phenyl-1-piperidin-4-yl-1,3-dihydro-2H-imidazol-2-one hydrochloride was added and the reaction refluxed overnight. The reaction was concentrated and purified by chromatography (silica gel, 0-5% methanol in methylene chloride containing 0.1% ammonium hydroxide, gradient elution), providing the title compound. MS 627.2464 (M+1)

Provenance & Evidence