Reaktion #45853

Reaktionsgleichung

dimethyl sulfoxide

(3S)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

4-cyano-N-ethyl-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

triethylamine

→

compound

Ausbeute 52.2%

4-Cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N-ethyl-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

Ausbeute 52.2%

Lösungsmittel

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Sonstigethe reaction liquid
3. 3
   Extraktionwas extracted with ethyl acetate
4. 4
   WaschenNext, the combined organic layer was washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenthe filtrate was concentrated under the reduced pressure
8. 8
   SonstigeThe resulting residue was purified by preparative TLC (eluent, dichloromethane

Vorschrift

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (80 μl, 633 μmol) was added at 140 to 150° C. to a dimethyl sulfoxide (10 ml) solution of 4-cyano-N-ethyl-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-285) (178 mg, 528 μmol) and triethylamine (96 μl, 686 μmol), followed by stirring at the same temperature for 165 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the combined organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under the reduced pressure. The resulting residue was purified by preparative TLC (eluent, dichloromethane:methanol=10:1, v/v) to obtain the entitled compound (119 mg, 52%) as an amorphous substance.

Quelle