Ammonia → HCID 68829543, compound

To a mixture of 2-{[3-cyano-4-(2-fluorophenyl)-2-isobutylquinolin-6-yl]oxy}acetamide (0.11 g, 0.29 mmol), 25% aqueous ammonia (2 ml), tetrahydrofuran (2 ml) and methanol (10 ml) was added Raney-nickel (1 ml), and the mixture was stirred under a hydrogen (0.5 MPa) atmosphere at room temperature for 6 hrs. The reaction mixture was filtered, and the filtrate was partitioned between ethyl acetate (50 ml) and 10% aqueous potassium carbonate solution (25 ml). The organic layer was washed with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give a colorless oil. This was dissolved in ethyl acetate (2 ml) and 4N solution of hydrogen chloride in ethyl acetate (1 ml) was added. The reaction mixture was concentrated and the obtained crude crystals were recrystallized from diisopropyl ether-methanol to give the title compound (0.078 g, yield 59%) as pale-yellow crystals.

1. filtrationThe reaction mixture was filtered
2. customthe filtrate was partitioned between ethyl acetate (50 ml) and 10% aqueous potassium carbonate solution (25 ml)
3. washThe organic layer was washed with saturated brine (10 ml)
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by silica gel column chromatography
7. customto give a colorless oil
8. concentrationThe reaction mixture was concentrated
9. customthe obtained crude crystals
10. customwere recrystallized from diisopropyl ether-methanol

ORD record

ord-8c80ca2acb4b4dc8839bb214514a7c1d

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547710B2