1,1'-Carbonyldiimidazole → (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Participants

Reaction Steps

36.5 g (235 mmol) of diallylglycine were dissolved in 165 ml of N,N-dimethylformamide and treated portionwise with 40.5 g (250 mmol) of 1,1'-carbonyldiimidazole. After stirring for 10 minutes 40 g (126 mmol) of (S)-8-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime were added and the mixture was stirred at room temperature for 1 hour and at 110° for 3.5 hours. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel while eluting with methylene chloride/ethyl acetate 1/1. There were obtained 27.1 g (45%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 181°-182.5°.

Provenance & Evidence