Reacción #45714

Ecuación de reacción

(3S)-3-(Dimethylamino)pyrrolidine

triethylamine

7-fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

Rendimiento 27.0%

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

Rendimiento 27.0%

Disolventes

dimethyl sulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe system was purged with nitrogen
2. 2
   Otrosealed up
3. 3
   TemperaturaAfter cooling
4. 4
   Otrothe solvent was evaporated away under reduced pressure
5. 5
   workup.DISSOLUTIONthe resulting residue was dissolved in chloroform
6. 6
   Lavadowashed with water
7. 7
   SecadoThe organic layer was dried over anhydrous sodium sulfate
8. 8
   Otrothe solvent was evaporated away under reduced pressure
9. 9
   Otrothe resulting residue was separated
10. 10
    Otropurified by preparative TLC
11. 11
    Otroto obtain a main product
12. 12
    LavadoThis was washed with a mixed solvent of isopropyl ether and ethanol
13. 13
    Filtraciónthe solid was collected by filtration

Procedimiento

(3S)-3-(Dimethylamino)pyrrolidine (53 μl, 0.42 mmol) and triethylamine (100 μl) were added to a dimethyl sulfoxide (2 ml) solution of 7-fluoro-5-methyl-2-(1-methyl-1H-pyrrol-2-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-166) (69 mg, 0.21 mmol). The system was purged with nitrogen, then sealed up, and heated at 110° C. for 3.5 hours. After cooling, the solvent was evaporated away under reduced pressure, the resulting residue was dissolved in chloroform and washed with water. The organic layer was dried over anhydrous sodium sulfate, then the solvent was evaporated away under reduced pressure, and the resulting residue was separated and purified by preparative TLC to obtain a main product. This was washed with a mixed solvent of isopropyl ether and ethanol, and the solid was collected by filtration to obtain the entitled compound (24 mg, 27%) as a colorless solid.

Fuente