Azetidine → HCID 57378180, compound

Participants

Reaction Steps

A mixture of 5-(2-(ethyl(methyl)amino)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid (144 mg, 419 μmol), azetidine (84.8 μl, 1.26 mmol), propylphosphonic anhydride (50% in ethyl acetate, 618 μl, 1.05 mmol) and N,N-diisopropylethylamine (214 μl, 1.26 mmol) in tetrahydrofuran (7 ml) was refluxed for 2.5 days (weekend). The solvent was evaporated, the residue was triturated with sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water and dried affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid [2-(ethyl-methylamino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (151 mg white solid, 94.1%) as a white solid. mp: 229-232° C., MS: m/z=383.1 (M+H+)

Provenance & Evidence