Methanol → HCID 66670377, compound

Participants

Reaction Steps

A 330 mg portion of 5-tert-butyl-N-(diaminomethylene)-1-[2-(2-methoxyphenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxamide was dissolved in 10 ml of dichloromethane, and 2.78 ml of a 1 M boron tribromide dichloromethane solution was added dropwise thereto at −70° C. under an atmosphere of argon, followed by stirring at room temperature for 14 hours. Under ice-cooling, 5 ml of methanol was added to the reaction liquid, and the reaction liquid was concentrated under a reduced pressure. The residue was subjected to three times of azeotropy with methanol, and a saturated sodium bicarbonate aqueous solution and saturated brine were added to the residue, followed by extraction with 20% methanol/chloroform. After drying the organic layer with anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (Chromatorex (registered trademark), methanol:chloroform=10:90). The resulting product was dissolved in 3 ml of ethanol and, under ice-cooling, 0.263 ml of 4 M hydrogen chloride/ethyl acetate was added, followed by stirring at room temperature for 15 hours. Then, the solid formed by adding ethyl acetate was collected by filtration to obtain 206 mg of 5-tert-butyl-N-(diaminomethylene)-1-[2-(2-hydroxyphenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxamide hydrochloride as a light brown solid.

Provenance & Evidence