Pyridine → HCID 23093504, compound

To a solution of bis(trichloromethyl)carbonate (0.43 g) in tetrahydrofuran (20 mL) was added dropwise a solution of pyridine (0.35 mL) in tetrahydrofuran (1 mL) under ice-cooling. The reaction solution was stirred for 10 minutes under ice-cooling, and 2-ethoxyethyl 2-(methylamino)ethyl carbonate hydrochloride (0.82 g) obtained in Reference Synthetic Example 48 was added thereto. A solution of triethylamine (0.60 mL) in tetrahydrofuran (1 mL) was added dropwise, and stirred at room temperature for 3 days. The reaction solution was concentrated under reduced pressure, and to the residue was added water (50 mL), and then extracted with ethyl acetate (50 mL). The ethyl acetate layer was washed with 0.2 N hydrochloric acid (20 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (20 mL). To the solution were added (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (1.11 g), triethylamine (0.63 mL) and 4-dimethylaminopyridine (0.037 g), and stirred at 60° C. for 6 hrs, and further at room temperature for 11 hrs. The reaction solution was concentrated under reduced pressure, and to the residue was added water (50 mL), and extracted with ethyl acetate (50 mL). The ethyl acetate layer was washed with saturated brine (50 mL), and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the residue was purified with basic silica gel column chromatography (eluted with ethyl acetate:hexane=3:7, then ethyl acetate:hexane=7:3) to give title compound as yellow amorphous solid (1.39 g).

1. temperaturecooling
2. temperaturecooling

ORD record

ord-5c36448a137b4d9f9e48f83b5112c509

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2