Tetrahydrofuran → N-[(3R)-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

3-Amino-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (25.6 mg, 0.0766 mmol) and p-nitrophenylchloroformate (15.3 mg, 0.0766 mmol) were dissolved in tetrahydrofuran (0.5 mL) under argon, and cooled to 0° C. Triethylamine (10.7 uL, 0.0766 mmol) was added and the reaction stirred for 1 h. Additional triethylamine was added (26.7 uL, 0.191 mmol) along with 3-(4-piperidinyl)quinolin-2-(1H)-one (17.5 mg, 0.0766 mmol). The reaction was warmed to room temperature and stirred overnight. The crude product was purified by reverse phase HPLC (C-18, 5% to 95% 0.1% trifluoroacetic acid/acetonitrile in 0.1% aqueous trifluoroacetic acid gradient elution) to give the title compound (30.2 mg). MS 588.2245 (M+1)

Provenance & Evidence