Dimethylformamide → HCID 86751230, compound

Participants

Reaction Steps

3.7 g (10 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo-[2,1-c][1,4]benzodiazepin-9-one, 30 ml of N,N-dimethylformamide, 4.27 ml (25 mmol) of N-ethyldiisopropylamine and 2.38 g (20 mmol) of propargyl bromide were stirred at room temperature for 1 hour. After evaporating the reaction solution the residue was chromatographed on 430 g of silica gel while eluting with ethyl acetate/methanol 9/1. The uniform fractions having the lower Rf were evaporated. There were obtained 1.19 g (29%) of (S)-8-chloro-11,12,13,13a-tetrahydro-1-(3-propargylamino-methyl-1,2,4-oxadiazol-5-yl)-9H-imidazo[1,5-a]pyrrolo-[2,1-c][1,4]benzodiazepin-9-one of m.p. 144°-145°, which was converted into the hydrochloride of m.p. 189°-192°.

Provenance & Evidence