تفاعل #332022
ord-fd2cd8463e294ccd9849cc724f8d443d
معادلة التفاعل
المتفاعلات
المذيبات
ظروف التفاعل
المعالجة
- 1أخرىA thick walled glass tube, equipped with a stir bar
- 2أخرىThe reaction mixture was purged with nitrogen
- 3أخرىthe tube was sealed
- 4درجة الحرارةThe reaction was maintained at 120° C. for 18 hours
- 5درجة الحرارةcooled to ambient temperature
- 6درجة الحرارةUpon cooling a precipitate
- 7أخرىformed
- 8أخرىThe remaining insoluble material was removed by filtration through a 0.2 micron PTFE membrane
- 9ترشيحfilter
- 10تركيزThe filtrate was concentrated under reduced pressure
- 11أخرىpurified by chromatography
- 12غسيلeluting with a 0-7% gradient of methanol in dichloromethane)
الإجراء التجريبي
A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (8 mg, 0.04 mmol), acetonitrile (50 mL), triethylamine (0.9 mL, 5.22 mmol), tri-o-tolylphosphine (30 mg, 0.10 mmol), N,N-dimethylacrylamide (189 mg, 1.91 mmol) and 1-{3-[8-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one (0.75 g, 1.7 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 120° C. in an oil bath. The reaction was maintained at 120° C. for 18 hours and then cooled to ambient temperature. Upon cooling a precipitate formed that was dissolved by the addition of methanol and chloroform. The remaining insoluble material was removed by filtration through a 0.2 micron PTFE membrane filter. The filtrate was concentrated under reduced pressure and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-7% gradient of methanol in dichloromethane) to provide 660 mg of 3-{2-(2-methoxyethyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-imidazo[4,5-c]quinolin-8-yl}-N,N-dimethylprop-2-enamide as an off-white solid.