o-Bis(bromomethyl)benzene → HCID 53858427, compound

Participants

Reaction Steps

1.5 g (4.65 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 20 ml of N,N-dimethylformamide, 4 ml (13.9 mmol) of N-ethyldiisopropylamine and 1.3 g (4.9 mmol) of α,α'-dibromo-o-xylene were stirred at room temperature for 1 hour. The reaction solution was evaporated, the residue was dissolved in methylene chloride and chromatographed on 50 g of silica gel while eluting with methylene chloride/ethyl acetate 1/1. There were obtained 1.2 g (61%) of (S)-12,12a-dihydro-1-(3-isoindolin-2-ylmethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 210°-213°.

Provenance & Evidence