4-(Tert-butylcarbamoyl)-2-methoxybenzenesulphonyl chloride → N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-prop-2-en-1-yl-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

Participants

Reaction Conditions

Reaction Steps

An amount of 231 mg (0.24 mmol) of the compound from Example 3A was suspended in 4 ml of tetrahydrofuran and cooled to −78° C. This suspension was admixed with stirring with 110 mg (0.981 mmol) of potassium tert-butylate. The mixture was allowed to warm to room temperature, and the solid dissolved. The reaction solution was stirred at room temperature for 10 minutes thereafter. Subsequently it was cooled again to −78° C. It was admixed with 300 mg (0.981 mmol) of 4-(tert-butylcarbamoyl)-2-methoxybenzenesulphonyl chloride (illustration as per Liotta et al., J. Org. Chem., 2001, 66, 3653-3661), the cooling bath was removed, and the solution was left with further stirring at room temperature overnight. The residue was admixed with water. 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 residue was purified by preparative HPLC (Method 6). This gave 275 mg (55% of theory) of the target compound.

Provenance & Evidence