Triethylamine → HCID 86673064, compound

Participants

Reaction Conditions

Reaction Steps

To a cold solution of 7-(3-Hydroxy-prop-1-ynyl)-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (example 54A) (230 mg, 0.577 mmol) and triethylamine (0.18 ml, 1.27 mmol) in dichloromethane (3 ml) was added dropwise methanesulfonyl chloride (90 μl, 1.15 mmol). The reaction mixture was stirred for 4 hours at 0° C. and poured onto a saturated solution of ammonium chloride. The product was extracted with dichloromethane, washed with brine, dried over sodium sulfate and concentrated to dryness. The residue methansulfonic ester was dissolved in acetone (3 ml) and treated with potassium carbonate (239 mg, 1.73 mmol) and methyl piperazine (87 mg, 0.866 mmol) and the mixture was stirred at 25° C. for 20 hours. The mixture was poured onto water and extracted with ethyl acetate, washed with water, brine, dried over sodium sulfate and absorbed over silica gel for purification by flash chromatography (ethyl acetate/methanol 90/10 then ethyl acetate/7N ammoniac in methanol: 90/10) to yield 2-isoquinolin-3-yl-7-[3-(4-methyl-piperazin-1-yl)-prop-1-ynyl]-chromen-4-one O-tert-butyl oxime (49 mg, 18%) as a brown solid.

Provenance & Evidence