Reacción #45778

Ecuación de reacción

(3S)-3-(Dimethylamino)pyrrolidine

triethylamine

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

→

compound

Rendimiento 69.4%

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

Rendimiento 69.4%

Disolventes

dimethyl sulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction liquid
2. 2
   Concentraciónwas concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in chloroform (100 ml)
4. 4
   Lavadowashed with water (50 ml) and saturated brine (50 ml)
5. 5
   SecadoAfter drying over anhydrous sodium sulfate and concentration
6. 6
   Otrothe residue was purified by silica gel column chromatography (eluent, chloroform/methanol=10:1)
7. 7
   Otrothe eluate was recrystallized from isopropanol

Procedimiento

(3S)-3-(Dimethylamino)pyrrolidine (123 μl, 0.970 mmol) and triethylamine (135 μl, 0.970 mmol) were added to a dimethyl sulfoxide (6 ml) solution of 7-fluoro-5-methyl-6-phenyl-2-(pyridin-3-yl)-1,3-benzoxazole-4-carbonitrile (I-209) (213 mg, 0.647 mmol), followed by stirring in an oil bath at 95° C. for 2 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in chloroform (100 ml), then washed with water (50 ml) and saturated brine (50 ml). After drying over anhydrous sodium sulfate and concentration, the residue was purified by silica gel column chromatography (eluent, chloroform/methanol=10:1), and the eluate was recrystallized from isopropanol to obtain the entitled compound (190 mg, 69.4%) as a yellow crystal.

Fuente