Benzyl 4-(4-(2-imino-2-methoxyethyl)pyridin-2-yl)piperazine-1-carboxylate → benzyl 4-(4-((2-methyl-5-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-2H-1,2,4-triazol-3-yl)methyl)pyridin-2-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 4-(4-(2-imino-2-methoxyethyl)pyridin-2-yl)piperazine-1-carboxylate (500 mg, 1.5 mmol) and TEA (1 mL, 7.5 mmol) in dry MeOH (5 mL), N′-methyl-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carbohydrazide (450 mg, 1.5 mmol) was added slowly at 0° C. The mixture was stirred at 80° C. for 3 h, and then concentrated to give the crude product, which was purified by reverse phase chromatography (Mobile phase: MeCN/H2O containing 0.01% TFA, 50%˜60%) to afford benzyl 4-(4-((2-methyl-5-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-2H-1,2,4-triazol-3-yl)methyl)pyridin-2-yl)piperazine-1-carboxylate as a white solid (280 mg, 27%). MS (ES+) C30H27F3N8O4 requires: 620, found: 621 [M+H]+.

Provenance & Evidence