[OH:1][CH:2]([C:13]1[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=1[F:21])[C:3]1[C:4]([CH3:12])=[CH:5][C:6]([C:9]([NH2:11])=[O:10])=[N:7][CH:8]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24].C(N(CC)CC)C.O>CN(C)C=O.C(OCC)(=O)C>[CH3:22][S:23]([O:1][CH:2]([C:3]1[CH:8]=[N:7][C:6]([C:9](=[O:10])[NH2:11])=[CH:5][C:4]=1[CH3:12])[C:13]1[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=1[F:21])(=[O:25])=[O:24]
To a solution of 5-[hydroxy(2,3,6-trifluorophenyl)methyl]-4-methylpyridine-2-carboxamide (7.11 g, 24.0 mmol) in N,N-dimethylformamide (150 ml), methanesulfonyl chloride (3.72 ml, 48.0 mmol) and then triethylamine (13.4 ml, 96.0 mmol) were added in a nitrogen atmosphere at 0° C., and the mixture was stirred for 2 hours at room temperature. Water and ethyl acetate were added to the reaction mixture at 0° C., the organic layer was separated, and the organic layer was washed sequentially with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography, and the fraction obtained from an elution with dichloromethane:methanol=49:1 was concentrated under reduced pressure, to obtain the title compound (4.71 g, 12.6 mmol, 52%) as a pale brown foamy substance.
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