Dimethylformamide → 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Participants

Reaction Steps

10.5 g (60 mmol) of BOC-glycine were dissolved in 50 ml of N,N-dimethylformamide, treated portionwise with 9.73 g (60 mmol) of 1,1'-carbonyldiimidazole and stirred at 55° for 20 minutes. After adding 15.5 g (57.1 mmol) of 5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime the mixture was stirred at 90° overnight. The reaction mixture was concentrated, the residue was dissolved in methylene chloride and the solution was washed three times with water. After drying the solution, evaporating the solvent and crystallizing the residue from ethanol there were obtained 20.4 g (87%) of 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 108°-113°.

Provenance & Evidence