Pyridine → HCID 23093457, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (10 mL) were added 3,4-difluorobenzoyl chloride (1.77 g) and pyridine (0.97 mL). After stirring at room temperature for 3 days, ethyl acetate (80 mL) was added to the reaction mixture. The mixture was washed with water (20 mL), a saturated aqueous sodium hydrogen carbonate solution (20 mL) and water (20 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 4 hrs, the mixture was concentrated under reduced pressure. The residue was washed with ethyl acetate (15 mL), and dried under reduced pressure at 60° C. to give the title compound (2.05 g) as a white solid. 1H-NMR (DMSO-d6): 2.62 (3H, s), 3.32 (2H, m), 4.53 (2H, t, J=5.0 Hz), 7.64 (1H, m), 8.00 (1H, m), 8.25 (1H, m), 9.25 (2H, bs).

1. washThe mixture was washed with water (20 mL)
2. dry with materiala saturated aqueous sodium hydrogen carbonate solution (20 mL) and water (20 mL), and dried over anhydrous magnesium sulfate
3. concentrationAfter concentration under reduced pressure
4. additiona 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue
5. stirringAfter stirring at room temperature for 4 hrs
6. concentrationthe mixture was concentrated under reduced pressure
7. washThe residue was washed with ethyl acetate (15 mL)
8. customdried under reduced pressure at 60° C.

ORD record

ord-4d1c3600a3e04cf7af81d0a93ad2d738

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08784885B2