Pyridine → 3-benzoylamino-N-{2,6-dimethyl-4-[2,2,2-trifluoro-1-(4-fluoro-phenyl)-1-hydroxy-ethyl]-phenyl}-benzamide

Temperature

20 °C

To a solution of 3-amino-N-{2,6-dimethyl-4-[2,2,2-trifluoro-1-(4-fluoro-phenyl)-1-hydroxy-ethyl]-phenyl}-benzamide (0.064 g, 0.15 mmol) (Example I4) in absolute dichloromethane (2 ml), at 20° C., was added a solution of benzoyl chloride (0.021 g, 0.15 mmol) in dichloromethane (0.5 ml). After 10 minutes, the suspension was treated with a solution of pyridine (0.016 g, 0.2 mmol) in dichloromethane (0.5 ml). The solution was stirred at 20° C. for 2 hours. The reaction mixture was quenched by addition of water (2 ml) and a few drops of aqueous hydrochloric acid (1M). The phases were separated and the aqueous phase was extracted with dichloromethane. The organic phases were dried over sodium sulfate, filtered through a plug silica gel which was further washed with ethyl acetate and concentrated. The residue was triturated in hexanes, filtered, washed with pentane and dried to yield the title compound as colorless crystals.

1. customat 20° C.
2. customThe reaction mixture was quenched by addition of water (2 ml) and a few drops of aqueous hydrochloric acid (1M)
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with dichloromethane
5. dry with materialThe organic phases were dried over sodium sulfate
6. filtrationfiltered through a plug silica gel which
7. washwas further washed with ethyl acetate
8. concentrationconcentrated
9. customThe residue was triturated in hexanes
10. filtrationfiltered
11. washwashed with pentane
12. customdried

ORD record

ord-1ff2215c6261440e9b1cb0e93f66df8b

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618173B2