C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[F:13][C:14]1[CH:24]=[CH:23][C:17]2[N:18]=[C:19]([CH2:21][OH:22])[S:20][C:16]=2[CH:15]=1.C(Cl)Cl>O>[F:13][C:14]1[CH:24]=[CH:23][C:17]2[N:18]=[C:19]([CH2:21][O:22][S:9]([CH3:8])(=[O:11])=[O:10])[S:20][C:16]=2[CH:15]=10.08 ml of triethylamine and 0.05 ml of methanesulfonyl chloride were added to a solution of 93.1 mg of 6-fluoro-2-hydroxymethylbenzothiazole [prepared as described in step (b) above] in 1.8 mi of methylene chloride cooled in an ice-water bath. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 1 hour. At the end of this time, water was added to the reaction mixture and the resulting mixture was extracted with methylene chloride. The resulting extract was washed consecutively with water and an aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 125.3 mg (yield 94%) of the title compound as a solid having a melting point of 68° to 72° C.
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