Trimethylaluminum → 4-(azetidine-1-carbonyl)-1-methyl-N-(8-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

To an argon purged solution of 8-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (60 mg, 268 μmol) in dioxane (5 ml) is added trimethylaluminum (2M solution in toluene, 401 μl, 803 μmol). The resulting mixture is stirred for 1 hour at 25° C., then ethyl 4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylate (63.5 mg, 268 μmol) is added, the mixture is heated to 100° C. and stirred for 72 hours. The crude material is loaded on silica and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 50-100% as eluent affording 4-(azetidine-1-carbonyl)-1-methyl-N-(8-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamide (77 mg, 69.3%) as a white solid. mp.: 243-5° C. MS: m/z=416.2 (M+H+).

Provenance & Evidence