Potassium Carbonate → 3-Cyano-N-(2,4-dimethoxybenzyl)-4-{[2-pyridazin-4-yl-4-(trifluoromethyl)phenyl]thio}-N-1,2,4-thiadiazol-5ylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

4-[2-Chloro-5-(trifluoromethyl)phenyl]pyridazine (Preparation 21, 0.050 g, 0.193 mmol), triisopropylsilanethiol (0.090 g, 472 mmol) and potassium carbonate (0.055 g, 0.398 mmol) were dissolved in N,N-dimethylacetamide (2 mL) in a Reactivial®. The reaction mixture was heated to 130° C. for 1 hour and 15 minutes. Then, the reaction was cooled to room temperature and 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 1, 0.085 g, 1.96 mmol) was added. The mixture was stirred at room temperature for thirty minutes. The reaction mixture was diluted in ethyl acetate (15 mL) and washed twice with a solution of saturated aqueous brine (15 mL). The aqueous layer was extracted with ethyl acetate (5 mL). The organic phases were combined and dried over sodium sulphate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ISCO™, 0-50% ethyl acetate in heptane gradient elution, 12 g SiO2) to give title compound as a yellow foam (0.095 g, 73%).

Provenance & Evidence