Chemical Compounds
a technology of chemical compounds and derivatives, applied in the field of sulfonamide derivatives, can solve the problems of increasing the risk of gout with increased sua levels
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example 1
4-(3-chloro-4-cyanophenoxy)-3-cyano-N-(5-fluoropyridin-2-yl)benzenesulfonamide
[0249]
3-Cyano-4-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Preparation 2, 10.5 g, 35.6 mmol) was added to a solution of 2-chloro-4-hydroxybenzonitrile (8.19 g, 53.3 mmol) and potassium carbonate (14.74 g, 106.7 mmol) in dimethylsulfoxide (100 mL) at room temperature. The resulting mixture was stirred at 80° C. for 44 hours. On cooling, the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution (200 mL) and ethyl acetate (1000 mL) was added. The aqueous layer was separated and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (3×200 mL), water (2×200 mL) and brine (2×200 mL). The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by reverse phase column chromatography eluting with acetonitrile (containing 0.1% HCO2H): water (containing 0.1% HCO2H) from 0 to 100% to afford the t...
example 99
4-(4-cyano-3-fluorophenoxy)-2-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide
[0278]
[0279]To a solution of 5-bromo-4-(4-cyano-3-fluorophenoxy)-N-(2,4-dimethoxybenzyl)-2-fluoro-N-(5-fluoropyridin-2-yl)benzenesulfonamide (Preparation 1, 220 mg, 0.35 mmol) in THF (8 mL), AcOH (10 mL) and water (2.5 mL) was added zinc dust (800 mg, 12.2 mmol). The reaction mixture was left to stir at room temperature for 70 hours. To the reaction mixture was added EtOAc (25 mL) and the mixture filtered through celite and washed with EtOAc (50 mL). The filtrate was retained and to this was added saturated aqueous NaHCO3 (80 mL). The organic layer was retained, dried over MgSO4, and the solvent removed in vacuo. The residue was purified using reverse phase column chromatography eluting with acetonitrile and water (acidic). The residue was dissolved in DCM and treated with TFA (0.3 mL) and stirred at room temperature for 1 hour. The reaction was concentrated in vacuo azeotroping with MeOH. The residue was...
example 100
4-(3-chloro-4-cyanophenoxy)-3-cyano-N-(pyridin-4-yl)benzenesulfonamide
[0281]
[0282]The title compound was prepared according to the method described for Example 101 using 4-aminopyridine.
[0283]MS m / z 411 [M+H]+
PUM
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