Reaktion #45757

Reaktionsgleichung

Ethyl [1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidin-3-yl]acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

→

compound

Ausbeute 41.4%

Ethyl (1-{4-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazol-2-yl}azetidin-3-yl)acetate

Ausbeute 41.4%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Einengenconcentration under reduced pressure, dilution with chloroform
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

Ethyl [1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidin-3-yl]acetate (I-190) (428 mg, 1.09 mmol) was dissolved in dimethyl sulfoxide (10 ml), then triethylamine (312 μl, 2.18 mmol) and (3S)-3-(dimethylamino)pyrrolidine (290 μl, 2.29 mmol) were added, followed by stirring in a sealed tube at 150° C. for 6 hours. After cooling, concentration under reduced pressure, dilution with chloroform, 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 (220 mg, 41.4%) as a white solid.

Quelle