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

To a solution of 1-(4-amino-3,5-dimethyl-phenyl)-2,2,2-trifluoro-1-(4-fluorophenyl)-ethanol (Example I3) (0.313 g, 1.0 mmol) in absolute dichloromethane (10 ml), at 20° C., was added sequentially a solution of 3-sulfinylamino-benzoyl chloride (0.201 g, 1.0 mmol) (the 3-sulfinylamino-benzoyl chloride was prepared in situ by refluxing 3-amino-benzoic acid in thionyl chloride) in absolute dichloromethane (1 ml) and a solution of pyridine (0.087 g, 1.1 mmol) in absolute dichloromethane (1 ml). After one hour, the reaction mixture was quenched by addition of water (0.5 ml) and aqueous hydrochloric acid (1M) (1 ml). After separation of the phases, the aqueous layer was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography over silica gel (eluent: ethyl acetate/hexanes 1:3 to 1:1). The title compound was isolated as colorless crystals.

1. customat 20° C.
2. customwas prepared in situ
3. customthe reaction mixture was quenched by addition of water (0.5 ml) and aqueous hydrochloric acid (1M) (1 ml)
4. customAfter separation of the phases
5. extractionthe aqueous layer was extracted with dichloromethane
6. dry with materialThe combined organic phases were dried over sodium sulfate
7. concentrationconcentrated
8. customThe residue was purified by column chromatography over silica gel (eluent: ethyl acetate/hexanes 1:3 to 1:1)

ORD record

ord-5025be649e2b49dfa61b30e6899271ec

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618173B2