Methanol → 5-{3-[(4-carbamimidoylphenylamino)-(5-fluoro-8-methoxychroman-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1H-pyrazole-4-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Iron powder (64 mg) was added to 6 ml of a methanol:water:acetic acid=1:1:1 mixed solvent solution containing 74 mg of 5-(3-{(5-fluoro-8-methoxychroman-6-yl)-[4-(5-trifluoromethyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-1H-pyrazole-4-carboxylic acid ethyl ester. The resulting mixture was stirred at 60° C. for 20 hours under a nitrogen atmosphere. After filtration, the reaction mixture was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give 22 mg of 5-{3-[(4-carbamimidoylphenylamino)-(5-fluoro-8-methoxychroman-6-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1H-pyrazole-4-carboxylic acid ethyl ester.

Provenance & Evidence