Hydrochloric Acid → N-(2-Methyl-3-(5-(5-(4-methylpiperazin-1-yl)pyridine-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

In a 25 mL, round-bottomed, single-necked flask equipped with a magnetic stirring bar and a condenser was placed N-(3-(6-methoxy-5-(5-(4-methylpiperazin-1-yl)pyridin-2-ylamino)pyridine-3-yl)-2-methylphenyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-carboxamide (18) (0.070 g, 0.13 mmol) and 3 N HCl (1 mL) in dioxane (3 mL). The reaction mixture was heated at 100° C. for 2 h. To this was added dichloromethane (10 mL) and H2O (10 mL), and the layers were separated. The aqueous phase was extracted with dichloromethane (3×5 mL), and the combined organic extracts were washed with H2O (5 mL) and brine (5 mL), dried (Na2SO4), and concentrated. The crude mixture was purified by column chromatography, gradient 0-33% MeOH in dichloromethane, to afford 0.053 g (80%) of N-(2-methyl-3-(5-(5-(4-methylpiperazin-1-yl)pyridine-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamide (19); Exact mass m/z 554.25; M=H m/z 555.20.

Provenance & Evidence