Dimethylformamide → HCID 54416509, compound

Participants

Reaction Steps

17.4 ml (1 00 mmol) of N-ethyldiisopropylamine and 7.87 ml (73 mmol) of butyl bromide were added to a solution of 4 g (12.18 mmol) of (S)-1-(5-aminomethyl-1,3,4-oxadiazol-2-yl)-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one in 100 ml of dimethylformamide whereupon the mixture was stirred at 70° for 12 hours. The dimethylformamide was evaporated and the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous phase was washed twice with methylene chloride and the organic phases were dried with sodium sulfate, filtered and evaporated. Chromatography (silica gel, ethyl acetate/methanol 10:1) yielded 2.1 g (39%) of (S)-1-(5-dibutylaminomethyl-1,3,4-oxadiazol-2-yl)-11,11a-dihydro-8H,10H-azeto-[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one as a colourless foam, Rf=0.4 (silica gel, ethyl acetate/methanol 10:1).

Provenance & Evidence