Dimethylformamide → 1-Methyl-4-trifluoromethyl-1h-pyrrole-3-carboxylic acid[2-(2-cyclopropylcyclobutyl)phenyl]amide

Participants

Reaction Steps

190 mg (1 mmol) 1-Methyl-trifluoromethyl-1H-pyrrole-3-carboxylic acid and 140 mg (1.05 mmol) oxalylic acid chloride were dissolved in 10 ml methylene chloride. The solution was stirred for 3 hours at room temperature in the presence of catalytic amounts of DMF. Then the resulting reaction mixture was slowly added to a solution consisting of 190 mg (1 mmol) 2-(2-cyclopropylcyclobutyl)phenylamine (prepared as described in Example 5), 200 mg (2 mmol) of triethylamine and 10 ml methylene chloride. After stirring for 16 hours at room temperature the solvent was distilled off and the raw material purified by flash chromatography over silica gel (eluant: hexane/methylene chloride/ethyl acetate 2:2:1). Yield: 240 mg (66% of theory) of 1-methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic acid [2-(2-cyclopropylcyclobutyl)phenyl]amide (cis-isomer) in the form of slightly yellow crystals (mp.: 167-169° C.).

Provenance & Evidence