Dimethylamine → HCID 58717241, compound

Participants

Reaction Steps

6-(4-Cyano-phenyl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.100 g, 0.240 mmol) was dissolved in 1:1 methanol/chloroform (20 mL), and hydrogen chloride gas was bubbled through the solution for 15 min, and it was then tightly capped and sealed. The reaction was stirred overnight at rt and then concentrated to dryness. The crude intermediate was dissolved in methanol (10 mL), and 2M dimethylamine (0.012 mL, 2.40 mmol) was added. The reaction was tightly capped and sealed and stirred overnight at rt. The reaction was concentrated and redissolved in methylene chloride (6 mL). Methanesulfonylchloride (0.03 mL, 0.360 mmol) and triethylamine (0.08 mL, 0.600 mmol) were added to the reaction. The reaction was stirred at rt overnight. The reaction was then concentrated and purified by flash chromatography using 0–100% ethyl acetate/hexanes as the eluent followed by methanol. The methanesulfonamide intermediate was dissolved in 5% ammonia/ethylene glycol and heated at 80° C. in a sealed tube for 2 hr. The reaction was quenched with water (50 mnL), extracted with ethyl acetate (3×50 mL), washed with brine (50 mL), dried with MgSO4, and concentrated. Purification by reverse phase HPLC and freeze-drying afforded the title compound (0.032 g, 26%): 1H NMR (CHCl3) δ 7.83–7.35 (m, 6H), 6.99–6.93 (m, 3H), 6.36 (bs, 1H), 4.18 (t, j=6.6 Hz, 2H), 3.83 (s, 3H), 3.37 (t, j=6.8 Hz, 2H), 3.19 (s, 3H), 2.93 (s, 3H), 2.81 (s, 3H) ppm; Mass Spec 511.3 (M+H)+.

Provenance & Evidence