Methyl propiolate → HCID 20060995, compound

Participants

Reaction Steps

A solution of 2-amino-7,8-dimethyl-4-[4-(2-methylimidazo-[4,5-c]pyrid-1-yl)phenyl]-3H-[1,5]benzodiazepine (Example 44) (395 mg, 1.0 mmol) and methyl propiolate (168 mg, 2.0 mmol) in n-butanol (4 ml) was heated at reflux for 16 hours under nitrogen. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (eluting with ethyl acetate:methanol: diethylamine=100:10:5). Fractions containing product were concentrated, and the residue was treated with dichloromethane, leaving some insoluble tarry material. The dichloromethane solution was decanted, concentrated, and the resulting brown solid triturated with hexane to give the title compound (46 mg, 10%), m.p. 192°-194° C.

Provenance & Evidence