Pyridine → HCID 23093561, compound

To a solution of bis(trichloromethyl) carbonate (0.652 g) in tetrahydrofuran (15 mL) was added dropwise a solution of pyridine (0.55 mL) in tetrahydrofuran (1 mL) under ice-cooling. The reaction solution was stirred for 30 minutes under ice-cooling, and 2-(methylamino)ethyl methoxyacetate (0.99 g) obtained in Reference Synthetic Example 13 was added. The reaction solution was stirred at room temperature for 3 hrs. The reaction solution was concentrated under reduced pressure, and to the residue were added ethyl acetate (80 mL) and water (50 mL), followed by stirring. The ethyl acetate layer was separated, and washed with saturated brine (30 mL), and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (15 mL). To the solution were added (R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (1.13 g), triethylamine (0.86 mL) and 4-dimethylaminopyridine (0.037 g), and stirred at 60° C. for 4 days. The reaction solution was concentrated under reduced pressure, and to the residue was added ethyl acetate (80 mL) and water (30 mL), followed by stirring. The ethyl acetate layer was separated, and washed with saturated aqueous solution of sodium bicarbonate (30 mL) and water (30 mL), and then, dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the residue was purified with silica gel column chromatography (eluted with ethyl acetate, then acetone:ethyl acetate=1:3), and further basic silica gel column chromatography (eluted with ethyl acetate:hexane=1:1, then 3:1) to give title compound as colorless sirup (0.588 g).

1. temperaturecooling
2. temperaturecooling

ORD record

ord-ec03674b43324a2f9409f4832cde226b

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2