1,1'-Carbonyldiimidazole → (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one

Participants

Reaction Steps

2.32 g (15 mmol) of diallylglycine were dissolved in 15 ml of N,N-dimethylformamide and treated with 2.75 g (17 mmol) of 1,1'-carbonyldiimidazole. After stirring at 50° C. for 20 minutes 3.01 (10 mmol) of (S)-7-fluoro-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 90° for 16 hours and at 120° for 2 hours. The solution was concentrated and the residue was purified by chromatography on 320 g of silica gel while eluting with ethyl acetate. There were obtained 1.54 g (37%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-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. 100°-105°.

Provenance & Evidence