Diisopropylethylamine → 4-(1,4-diaza-bicyclo[3.2.1]octane-4-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide

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Reaction Conditions

Reaction Steps

A mixture of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (100 mg, 276 μmol), 1,4-diazabicyclo[3.2.1]octane dihydrochloride (102 mg, 552 μmol), propylphosphonic anhydride (50% in ethyl acetate, 407 μl, 690 μmol) and N,N-diisopropylethylamine (469 μl, 2.76 mmol) in tetrahydrofuran (4.5 ml) was stirred overnight at 25° C. The mixture was applied on basic silica gel and purified by column chromatography using dichloromethane/methanol 19:1 as eluent to give 4-(1,4-diaza-bicyclo[3.2.1]octane-4-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide (45 mg, 35.7%) as a white solid. mp: 110.1, MS: m/z=457.2 (M+H+).

Provenance & Evidence