Ammonium Chloride → HCID 68289689, compound

Participants

Reaction Steps

To a solution of sodium 4-({(4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)-benzyl]amino}sulfonyl)benzoate (100 mg, 0.186 mmol) prepared in Example 2, ammonium chloride (50 mg, 0.929 mmol) and N,N-diisopropylethylamine (162 μL, 0.929 mmol) in N,N-dimethylacetamide (1.8 mL) was added 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate methanaminium (85 mg, 0.223 mmol) at 0° C., and the mixture was stirred at room temperature overnight. To the reaction solution was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, washed with water twice, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0→91:9) to give 4-({(4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)benzyl]amino}sulfonyl)benzamide (26 mg, 27%) as a colorless powder.

Provenance & Evidence