Reacción #45667

Ecuación de reacción

dimethyl sulfoxide

(3R)-3-(dimethylamino)pyrrolidine

dimethyl sulfoxide

N-[2-(tert-butyldiphenylsiloxy)ethyl]-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

triethylamine

→

compound

Rendimiento 42.0%

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

Rendimiento 42.0%

Disolventes

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction liquid
2. 2
   Extracciónwas extracted with ethyl acetate
3. 3
   LavadoNext, the combined organic layer was washed with saturated brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónthe filtrate was concentrated under reduced pressure

Procedimiento

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3R)-3-(dimethylamino)pyrrolidine (76 μl, 598 μmol) was added at 150° C. to a dimethyl sulfoxide (9 ml) solution of N-[2-(tert-butyldiphenylsiloxy)ethyl]-4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-124) (295 mg, 499 μmol) and triethylamine (90 μl, 649 μmol), followed by stirring at the same temperature for 20 minutes. After pooling, 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, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (10:1, v/v) gave the entitled compound (93 mg, 42%) as an amorphous substance.

Fuente