Imidazole → HCID 13505203, compound

Participants

Reaction Steps

1.36 g (20 mmol) of imidazole is combined in 15 ml of absolute tetrahydrofuran with 0.36 ml of thionyl chloride in 5 ml of absolute tetrahydrofuran. After 15 minutes of agitation at room temperature, the mixture is suctioned off from the precipitate. The filtrate is added to a solution of 0.33 g (1.08 mmol) of 6-(1-cyclohexen-4-yl)-4-methyl-β-carboline-3-carboxylic acid in 15 ml of absolute dimethylformamide. After agitation for one hour at room temperature, the mixture is combined with 1.15 g (13 mmol) of propionamidoxime, the tetrahydrofuran is distilled off, and the reaction solution is heated for 3 hours under reflux. After the solvent has been removed by distillation, the mixture is distributed in methylene chloride/saturated sodium bicarbonate solution, the organic phase is washed with saturated sodium chloride solution until it is neutral, dried over magnesium sulfate, filtered, and concentrated to dryness. After column chromatography over silica gel with methylene chloride:ethanol=10:1 as the eluent, and recrystallization from ethanol/hexane, the residue yields 194 mg (50% of theory) of 6-(1-cyclohexen-4-yl)-4-methyl-3-(3-ethyl-1,2,4-oxadiazol-5-yl)-β-carboline, mp 247°-248° C.

Provenance & Evidence