Dimethyl Sulfoxide → HCID 15952466, compound

Participants

Reaction Steps

To a solution of 2,2,2-trichloro-1-[10-(4-iodo-3-methylbenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]ethanone of Step B (1 g, 1.74 mmol) in dry acetonitrile (30 mL) at room temperature under nitrogen was added dimethyl sulfoxide (0.62 mL, 8.72 mmol) followed by 3-(aminomethyl)pyridine (0.36 mL, 3.49 mmol) and the reaction mixture heated to reflux for 36 hours. The cooled reaction mixture was concentrated in vacuo to a small volume then partitioned between ethyl acetate (50 mL) and 1 M sodium hydroxide (50 mL). The organic layer was separated, washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a yellow foam. Purification by flash chromatography using ethyl acetate as solvent afforded a white foam (0.94 g). Recrystallization from ethyl acetate/hexane gave the title compound (0.77 g, 79%) as white solid, m.p. 176-177° C.

Provenance & Evidence