1,1'-Carbonyldiimidazole → 4-{-4-Methyl-5-[2-(trifluoromethyl)phenyl]-4h-1,2,4-triazol-3-yl}-n'-(4,4,4-trifluoro-2-methylbutanoyl)bicyclo[2.2.2]octane-1-carbohydrazide

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Reaction Steps

A solution of 2-methyl-4,4,4-trifluorobutyric acid (108 mg, 0.692 mmol) and 1,1′-carbonyldiimidazole (101 mg, 0.623 mmol) in DMF (1 ml) was stirred at room temperature under a nitrogen atmosphere. After 30 min, compound 13-A (100 mg, 0.254 mmol) was added and the solution stirred overnight. DMF was removed in vacuo and the solid was redissolved in CH3CN (4 ml). Product was purified by Gilson reverse phase chromatography eluting with a 10-90% CH3CN (0.1% TFA)/water (0.1% TFA) gradient. Solvent was removed in vacuo and the product free based from methylene chloride and saturated aqueous sodium bicarbonate. The organic layer was dried over MgSO4 and the solvent removed to yield 13-B as a white solid. MS (ESI+)=532.18 (M+1).

Provenance & Evidence