Pyridine → HCID 23093483, compound

To a solution of bis(trichloromethyl)carbonate (1.19 g) in tetrahydrofuran (40 mL) was added dropwise a solution of pyridine (0.95 mL) in tetrahydrofuran (2 mL) under ice-cooling. The reaction solution was stirred for 30 minutes under ice-cooling, and 3-(methylamino)propyl acetate hydrochloride (1.90 g) obtained in Reference Synthetic Example 42 was added thereto. A solution of triethylamine (1.68 mL) in tetrahydrofuran (2 mL) was added dropwise, and stirred at room temperature for 3 hrs. The reaction solution was concentrated under reduced pressure, and to the residue was added water (100 mL), and then extracted with ethyl acetate (100 mL). The ethyl acetate layer was washed with saturated brine (100 mL), and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (40 mL). To the solution were added (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (1.99 g), triethylamine (1.50 mL) and 4-dimethylaminopyridine (catalytic amount), and stirred at 60° C. overnight. The reaction solution was concentrated under reduced pressure, and to the residue was added water (100 mL), and extracted with ethyl acetate (100 mL). The ethyl acetate layer was washed with saturated brine (100 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=1:2, then 1:1) to give title compound as yellow amorphous solid (1.22 g).

1. temperaturecooling
2. temperaturecooling

ORD record

ord-04d3c83e9e914a59b8ff34cb6a924e5d

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2