Reaktion #45592

Reaktionsgleichung

sodium bicarbonate water

(3S)-3-(Dimethylamino)pyrrolidine

7-fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

Ausbeute 17.0%

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

Ausbeute 17.0%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Extraktionfollowed by extraction three times with ethyl acetate
3. 3
   Waschenthe organic layer was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   FiltrationAfter filtration and concentration under reduced pressure
6. 6
   Einengenthe eluate with chloroform:methanol (50:1) was concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
8. 8
   Waschenwashed twice with saturated brine
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    FiltrationAfter filtration and concentration tinder reduced pressure

Vorschrift

(3S)-3-(Dimethylamino)pyrrolidine (76 μl, 0.60 mmol) was added to a dimethyl sulfoxide (4 ml) solution of 7-fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-59) (58 mg, 0.20 mmol), followed by stirring at 90° C. for 1 hour. After cooling to room temperature, the above brown oily substance and saturated sodium bicarbonate water were added, followed by extraction three times with ethyl acetate, the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform:methanol (50:1) was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed twice with saturated brine, then dried over anhydrous magnesium sulfate. After filtration and concentration tinder reduced pressure, the entitled compound (39 mg, 17%) was obtained as a brown oily substance.

Quelle