Sodium Carbonate → 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxothiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide

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Reaction Steps

2-(3,5-Bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide can be produced by suspending 2-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-[4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-isobutyramide in methanol and treating it at room temperature with oxone™ (potassium peroxymonosulfate). The suspension is then stirred for about 16 hours at room temperature and cooled to about 0° C., followed by the dropwise addition of sodium hydrogen sulfite solution. After stirring at room temperature, the pH is adjusted to about 8.5 with saturated aqueous sodium carbonate. The methanol is then evaporated under reduced pressure, and the residue is extracted with dichloromethane. The organic phase is washed with half-saturated aqueous sodium chloride. The solvent is exchanged under reduced pressure in a rotary evaporator with isopropanol, and the volume reduced. The solution is cooled to room temperature under stirring and stirred further for about 1 hour. The precipitate formed is filtered off, washed with isopropanol, and dried under high vacuum to yield 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxothiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide as a white powder.

Provenance & Evidence