반응 #45688

반응 방정식

7-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

solid

수율 44.3%

7-[(3S)-3-(Dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile

수율 44.3%

용매

dimethyl sulfoxide

dichloromethane

반응 조건

후처리

1. 1
   세척washed with water and saturated brine
2. 2
   건조dried over anhydrous sodium sulfate
3. 3
   기타The solvent was evaporated away under reduced pressure
4. 4
   기타the resulting residue was purified by silica gel column chromatography (silica gel 10 g, dichloromethane:methanol=30:1)
5. 5
   workup.ADDITIONisopropyl ether was added
6. 6
   여과the insoluble matter was collected by filtration

실험 절차

7-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-yl)-1,3-benzoxazole-4-carbonitrile (I-136) (0.21 g, 0.63 mmol) was suspended in dimethyl sulfoxide (5 ml), then triethylamine (0.91 ml, 1.37 mmol) and (3S)-3-(dimethylamino)pyrrolidine (0.16 ml, 1.26 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours. This was diluted with dichloromethane, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (silica gel 10 g, dichloromethane:methanol=30:1) and preparative thin-layer chromatography (dichloromethane:methanol=20:1), then isopropyl ether was added, and the insoluble matter was collected by filtration to obtain a beige solid (0.12 g, 44%).

출처