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

HRID 17314

Reaktionsgleichung

Reaktionsgleichung von HRID 17314
[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.F[C:10]1[C:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:12]([CH3:24])[C:13]([C:22]#[N:23])=[C:14]2[C:18]=1[O:17][C:16]([CH2:19][O:20][CH3:21])=[N:15]2.O.C(=O)(O)[O-].[Na+]>CS(C)=O>[CH3:1][N:2]([CH3:8])[C@H:3]1[CH2:7][CH2:6][N:5]([C:10]2[C:11]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:12]([CH3:24])[C:13]([C:22]#[N:23])=[C:14]3[C:18]=2[O:17][C:16]([CH2:19][O:20][CH3:21])=[N:15]3)[CH2:4]1

Komponenten

5

Edukt 3

HCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685851157-Fluoro-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileHCID 86585896Sodium bicarbonate water

Produkt 1

HCID 685844727-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-2-(methoxymethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(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.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction three times with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. concentrationthe eluate with chloroform:methanol (50:1) was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed twice with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter filtration and concentration tinder reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b341d755573047dcac0d67357cf083fb
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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