Triethylamine → 7-[(3S)-3-(Dimethylamino)-1-pyrrolidinyl]-2-(3-hydroxy-3-methylazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile
Reaktionsgleichung
F[C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]2[C:10]=1[O:9][C:8]([N:11]1[CH2:14][C:13]([OH:16])([CH3:15])[CH2:12]1)=[N:7]2.C(N(CC)CC)C.[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][NH:37][CH2:36]1>CS(C)=O>[CH3:33][N:34]([CH3:40])[C@H:35]1[CH2:39][CH2:38][N:37]([C:2]2[C:3]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:4]([CH3:19])[C:5]([C:17]#[N:18])=[C:6]3[C:10]=2[O:9][C:8]([N:11]2[CH2:14][C:13]([OH:16])([CH3:15])[CH2:12]2)=[N:7]3)[CH2:36]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
7-Fluoro-2-(3-hydroxy-3-methylazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-193) (230 mg, 0.68 mmol) was dissolved in DMSO (5 ml), then triethylamine (195 μl, 1.36 mmol) and (3S)-3-(dimethylamino)pyrrolidine (181 μl, 1.43 mmol) were added, followed by stirring at 150° C. for 4 hours. After cooling, concentration under reduced pressure, dilution with ethyl acetate and washing with water, the organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (32 mg, 11%) as a white solid.
Aufarbeitung
- temperatureAfter cooling
- concentrationconcentration under reduced pressure, dilution with ethyl acetate
- washwashing with water
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated away under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-f508cb8052fa41a6ba4570e357ba2f54
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07737166B2
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