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

Temperature

100 °C

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.

1. customIn a 25 mL, round-bottomed, single-necked flask equipped with a magnetic stirring bar and a condenser
2. customthe layers were separated
3. extractionThe aqueous phase was extracted with dichloromethane (3×5 mL)
4. washthe combined organic extracts were washed with H2O (5 mL) and brine (5 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe crude mixture was purified by column chromatography, gradient 0-33% MeOH in dichloromethane

ORD record

ord-8b74d8558076403893ff4687b84a3ae9

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058446B2