Reaktion #45760

Reaktionsgleichung

7-Fluoro-2-[3-(hydroxymethyl)azetidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

compound

Ausbeute 130.3%

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

Ausbeute 130.3%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Einengenconcentration under reduced pressure, dilution with methylene chloride
3. 3
   Waschenwashing with water
4. 4
   Trocknenthe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was evaporated away under reduced pressure

Vorschrift

7-Fluoro-2-[3-(hydroxymethyl)azetidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-192) (220 mg, 0.37 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (166 μl, 1.19 mmol) and (3S)-3-(dimethylamino)pyrrolidine (159 μl, 1.25 mmol) were added, followed by stirring in a sealed tube at 150° C. for 19 hours. After cooling, concentration under reduced pressure, dilution with methylene chloride 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 preparative silica gel column chromatography. The eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (208 mg, 74%) as a white amorphous substance.

Quelle