Triethylamine → 4-{5-[1-(4-chlorophenyl)cyclopropyl]-4-methyl-4H-1,2,4-triazol-3-yl}cyclohexanol

Participants

Reaction Conditions

Reaction Steps

Methyl trifluoromethanesulfonate (53.9 μL, 0.491 mmol) was added to 1-(4-chlorophenyl)-N-methylcyclopropanecarboxamide (100.0 mg, 0.48 mmol). The resulting reaction mixture was stirred at 60° C. for 30 min. To the reaction mixture were then added toluene (2.0 mL), triethylamine (68.6 μL, 0.492 mmol) and 4-hydroxycyclohexanecarbo-hydrazide (38 mg, 0.24 mmol). The resulting mixture was stirred for 3 h at 60° C. and an additional 1 h. at 110° C. The mixture was then cooled to room temperature (about 25° C.). After cooling, the reaction mixture was concentrated to provide a residue. The residue was purified by Prep-HPLC to afford the desired products (cis- and trans-two isomers). Isomer I: LCMS: (M+H)+=332.2/334.2; isomer II: LCMS: (M+H)+=332.1/334.1.

Provenance & Evidence