Carbon Dioxide → (S)-8-chloro-1-(5-dimethylaminomethyl-1,2.4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-one

Participants

Reaction Steps

1.4 g (13.5 mmol) of N,N-dimethylglycine were dissolved in 20 ml of N,N-dimethylformamide and treated portionwise with 2.6 g (15 mmol) of 1,1'-carbonyldiimidazole. After completion of the CO2 elimination the solution was stirred at 70° for 30'. Then, 4.02 g (15 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime were added and the mixture was stirred at 90° overnight. By evaporation of the solution and chromatography of the residue on 340 g of silica gel while eluting with methylene chloride/methanol 19/1 there were obtained 1.99 g (40%) of (S)-8-chloro-1-(5-dimethylaminomethyl-1,2.4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]-benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 261°.

Provenance & Evidence