Water → 4''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid (4-nitro-phenyl)-amide

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Reaction Steps

To a mixture of 5-n-butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-4-one (100 mg, 0.19 mmol) (from Example 16, Step C) and sodium hydride (4.5 mg, 0.19 mmol) in DMF, (0.5 mL) which had been stirring at room temperature for 2 h, was added dropwise a solution of 4-fluoro-nitrobenzene (27 mg, 0.19 mmol) dissolved in 0.3 mL DMF. The yellow reaction mixture was stirred at 60° C. for 29 hours. After cooling to room temperature, water and EtOAc were added and the phases were separated. After two more extractions with EtOAc, the organic layers were combined and washed twice with water, and brine, and then dried over Na2SO4. The crude product obtained after filtration and evaporation of volatiles was flash chromatographed over silica gel (gradient elution using 0.3-5.0% MeOH/CH2Cl2) to afford 53 mg (43%) of the title compound as an off-white solid, homogeneous by TLC in 5% MeOH/CH2Cl2 ; mass spectrum (FAB) m/e 652 (M+1)+ ; mp 186°-187° C.

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