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

HRID 17406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17406
[N:1]1([C:5]2[O:6][C:7]3[C:8](=[C:10]([C:22]#[N:23])[C:11]([CH3:21])=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:13]=3F)[N:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:24]([N:26]([CH2:29]C)[CH2:27][CH3:28])C.[NH:31]1CC[CH2:33][CH2:32]1>CS(C)=O.ClCCl>[N:1]1([C:5]2[O:6][C:7]3[C:8](=[C:10]([C:22]#[N:23])[C:11]([CH3:21])=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:13]=3[N:31]3[CH2:32][CH2:33][C@H:27]([N:26]([CH3:24])[CH3:29])[CH2:28]3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 685856232-(Azetidin-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Produkt 1

HCID 685846442-(azetidin-1-yl)-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2-(Azetidin-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-134) (0.11 g, 0.36 mmol) was dissolved in dimethyl sulfoxide (3.5 ml), then triethylamine (0.10 ml, 0.72 mmol) and (3S)-3-dimethylamino)pyrrolidine (92.0 μl, 0.73 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 diisopropyl ether was added, and the insoluble matter was collected by filtration to obtain a pale beige solid (23 mg, 17%).

Aufarbeitung

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=20:1)
  5. additiondiisopropyl ether was added
  6. filtrationthe insoluble matter was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-dd66c21ae78448029bbd4b0f2bc20496
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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