Pyridine → 3-(4-Piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrol-6-yl-methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-piperidin-1-ylmethyl-phenyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-6-amine (82.1 mg, 0.230 mmol) in pyridine (8.2 mL) was treated with methanesulfonyl chloride (58.7 μL, 0.758 mmol) and heated at 50° C. for 15 h. The cooled reaction mixture was treated with saturated sodium bicarbonate solution and diluted with 20% MeOH in DCM and water. The layers were separated, the aqueous phase extracted into 20% MeOH in DCM, and the combined organic phases were dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by preparative HPLC (0-30% MeCN in water (0.1% formic acid) over 30 min, 35 mL/min) to afford the title compound as a tan solid (38 mg, 38%). 1H NMR (DMSO-D6, 400 MHz): 12.03 (s, 1H), 8.96 (d, J=2.1 Hz, 1H), 8.88 (d, J=2.1 Hz, 1H), 8.64 (s, 1H), 7.85 (s, 1H), 7.77 (d, J=8.1 Hz, 2H), 7.42 (d, J=8.1 Hz, 2H), 3.48 (s, 2H), 3.22 (s, 3H), 2.36 (m, 4H), 1.55-1.46 (m, 4H), 1.41 (m, 2H). LCMS (Method D): RT=7.37 min, M+H+=436.

Provenance & Evidence