Dimethyl Sulfoxide → HCID 10301874, compound

Participants

Reaction Steps

To a solution of 2,2,2-trichloro-1-{10-[(2,2′-dimethyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Step D (8.0 g, 15 mmol) and dimethyl sulfoxide (5.3 mL, 75 mmol) in dry acetonitrile (90 mL) at room temperature under nitrogen was added 3-(aminomethyl)pyridine (3.1 mL, 30 mmol) and the reaction mixture was heated to reflux for 48 hours. The cooled mixture was concentrated in vacuo, the oily residue redissolved in ethyl acetate (400 mL), washed with 1M sodium hydroxide (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a red foam. Purification by flash chromatography using a solvent gradient of 50 to 100% ethyl acetate in hexane gave a pale yellow foam. Trituration with hot diethyl ether (150 mL) afforded the title compound (5.9 g, 75%) as a pale yellow solid, m.p. 147-149° C. Alternatively, the title compound could be purified by HPLC (normal phase, Luna CN bonded packing) and crystallized from ethyl acetate/hexane, m.p. 148-150° C.

Provenance & Evidence