Tetrahydrofuran → 4-{[Cyclohexyl(3-methylthieno[2,3-b]pyridin-2-yl)methyl]amino}benzoic acid

To a mixture of methyl 4-{[cyclohexyl(3-methylthieno[2,3-b]pyridin-2-yl)methyl]amino}benzoate (975 mg) synthesized above, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred overnight with heating under reflux, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), 1N hydrochloric acid (10 mL) was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (701 mg, 75%) as a pale-yellow solid.

1. temperaturewith heating
2. temperatureunder reflux
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in water (20 mL)
5. addition1N hydrochloric acid (10 mL) was added
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)

ORD record

ord-f8dedcd06ced4658a52004b0dea47767

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2