Cesium carbonate → N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

Participants

Reaction Conditions

Reaction Steps

An amount of 50 mg (0.108 mmol) of N-tert-butyl-4-{[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide from Example 14 and 53 mg (0.161 mmol) of caesium carbonate were suspended in 1 ml of dimethylformamide and admixed with 26 μl (0.161 mmol) of 3-bromo-1,1,1-trifluoro-2-propanol. The mixture was stirred at 75° C. for 8 hours. The suspension was diluted with saturated aqueous ammonium chloride solution. It was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. The crude product was purified by preparative HPLC [Method 5]. This gave 22 mg (36% of theory) of the target compound.

Provenance & Evidence