Reaktion #45686

Reaktionsgleichung

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

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

solid

Ausbeute 29.5%

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

Ausbeute 29.5%

Lösungsmittel

dimethyl sulfoxide

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water and saturated brine
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   SonstigeThe solvent was evaporated away under reduced pressure
4. 4
   Sonstigethe resulting residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=20:1)
5. 5
   workup.ADDITIONether and a small amount of hexane were added
6. 6
   Filtrationthe insoluble matter was collected by filtration

Vorschrift

7-Fluoro-5-methyl-6-phenyl-2-(pyrrolidin-1-yl)-1,3-benzoxazole-4-carbonitrile (I-135) (0.10 g, 0.31 mmol) was suspended in dimethyl sulfoxide (3.5 ml), then triethylamine (90.0 μl, 0.65 mmol) and (3S)-3-(dimethylamino)pyrrolidine (88.0 μl, 0.69 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 preparative thin-layer chromatography (dichloromethane:methanol=20:1), then ether and a small amount of hexane were added, and the insoluble matter was collected by filtration to obtain a beige solid (38 mg, 29%).

Quelle