Reacción #45854

Ecuación de reacción

dimethyl sulfoxide

(3S)-3-(methylamino)pyrrolidine

dimethyl sulfoxide

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

triethylamine

→

compound

Rendimiento 32.2%

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

Rendimiento 32.2%

Disolventes

brine

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Otrothe reaction liquid
3. 3
   Extracciónwas extracted with ethyl acetate
4. 4
   LavadoNext, the combined organic layer was washed with saturated brine
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónthe filtrate was concentrated under the reduced pressure
8. 8
   OtroThe resulting residue was purified by preparative TLC (eluent, dichloromethane

Procedimiento

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3S)-3-(methylamino)pyrrolidine (67 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 160 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 (71 mg, 32%) as an amorphous substance.

Fuente