Reaktion #45697

Reaktionsgleichung

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

(3S)-3-(dimethylamino)pyrrolidine

triethylamine

→

compound

Ausbeute 23.6%

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

Ausbeute 23.6%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Waschenfractionation with water and ethyl acetate, the organic layer was washed with saturated brine
3. 3
   TrocknenThe obtained organic layer was dried over anhydrous sodium sulfate
4. 4
   Sonstigethe solvent was evaporated away under reduced pressure
5. 5
   WaschenElution with a mixed solvent of chloroform/methanol (9:1, v/v/)

Vorschrift

7-Fluoro-2-(3-hydroxyazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-143) (120 mg, 0.37 mmol) was dissolved in dimethyl sulfoxide (6 ml), then (3S)-3-(dimethylamino)pyrrolidine (71 μl, 0.56 mmol) and triethylamine (189 μl, 1.11 mmol) were added, followed by stirring at 150° C. under nitrogen atmosphere for 5 hours. After cooling and fractionation with water and ethyl acetate, the organic layer was washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (9:1, v/v/) gave the entitled compound (36.4 mg, 23%) as a white solid.

Quelle