反应详情

温度

100 °C

A suspension of N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.21 gm) from Preparation No. 40 and cesium carbonate (0.33 gm) in DMF (2 mL) is treated with α,4-dichloroanisole (0.13 gm). The mixture is tightly capped and heated to 100° C. for 3 hrs. The reaction mixture is allowed to cool to room temperature, diluted with dichloromethane (50 mL) and washed with water. The aqueous phase is extracted with two additional portions of dichloromethane. The combined organic phase is washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 1% to 4% methanol in dichloromethane and then by recrystallization with acetonitrile to afford 0.20 gm of the title compound as a white solid.

1. customfrom Preparation No
2. customThe mixture is tightly capped
3. temperatureto cool to room temperature
4. washwashed with water
5. extractionThe aqueous phase is extracted with two additional portions of dichloromethane
6. washThe combined organic phase is washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure
9. customThe crude product is purified by flash column chromatography
10. washeluting with 1% to 4% methanol in dichloromethane
11. customby recrystallization with acetonitrile