反应详情

温度

50 °C

Potassium carbonate (530 mg, 3.84 mmol), morpholine (92 mg, 1.06 mmol), and 8-(3-chloropropoxy)-2-methoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (350 mg, 0.96 mmol) were added to 15 mL of DMF and heated to 50° C. for 18 hours. Analysis by LC/MS indicated the presence of two peaks and the reaction mixture was cooled and poured into 500 mL of deionized water. After three hours, no precipitation was observed. Sodium chloride (250 g) was added to the mixture and the mixture was stirred vigorously overnight. The precipitate was collected by filtration, dissolved in dichloromethane, and purified by chromatography on a HORIZON HPFC system (eluting with a gradient of methanol/dichloromethane (20:80) in dichloromethane from 0:100 to 40:60). The resulting material was concentrated under reduced pressure, crystallized from acetonitrile, and dried under high vacuum to yield 36 mg of 2-methoxymethyl-8-(3-morpholin-4-ylpropoxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine as tan crystals, mp 193-196° C.

1. temperaturethe reaction mixture was cooled
2. customno precipitation
3. additionSodium chloride (250 g) was added to the mixture
4. filtrationThe precipitate was collected by filtration
5. dissolutiondissolved in dichloromethane
6. custompurified by chromatography on a HORIZON HPFC system (
7. washeluting with a gradient of methanol/dichloromethane (20:80) in dichloromethane from 0:100 to 40:60)
8. concentrationThe resulting material was concentrated under reduced pressure
9. customcrystallized from acetonitrile
10. customdried under high vacuum