Ethanol → 4-{[(5-Chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoic acid

To a mixture of methyl 4-{[(5-chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methyl]amino}benzoate (1.31 g) synthesized above, ethanol (20 mL) and tetrahydrofuran (20 mL) was added 1N lithium hydroxide aqueous solution (20 mL), and the mixture was stirred with heating under reflux for 3 hr, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), and 1N hydrochloric acid (20 mL) was added at 0° C. The resulting precipitate was collected by filtration and the obtained solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (1.21 g, 96%) as a pale-yellow solid.

1. temperaturewith heating
2. temperatureunder reflux for 3 hr
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in water (40 mL)
5. addition1N hydrochloric acid (20 mL) was added at 0° C
6. filtrationThe resulting precipitate was collected by filtration
7. dissolutionthe obtained solid was dissolved in ethyl acetate
8. washThe solution was washed with saturated brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. washThe residue was washed with diisopropyl ether

ORD-Eintrag

ord-99c67d7d0f684cac942b117453f36945

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08436043B2