Reacción #45857

Ecuación de reacción

(3S)-3-(Ethylamino)pyrrolidine

triethylamine

2-cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

Rendimiento 23.5%

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

Rendimiento 23.5%

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 ethyl acetate
4. 4
   Lavadowashed with water and saturated brine
5. 5
   SecadoAfter drying over anhydrous sodium sulfate
6. 6
   Otrothe insoluble matter was separated by filtration
7. 7
   Otrothe residue obtained by concentration
8. 8
   Otrowas purified by preparative TLC (eluent, chloroform
9. 9
   Otromethanol=10:1, v/v), and the obtained eluate was purified in slurry with isopropyl ether

Procedimiento

(3S)-3-(Ethylamino)pyrrolidine (85 μl, 0.684 mmol) and triethylamine (95 μl, 0.684 mmol) were added to a dimethyl sulfoxide (2 ml) solution of 2-cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (100 mg, 0.342 mmol), followed by stirring in an oil bath at 95° C. for 3 hours. The reaction liquid was concentrated under reduced pressure, then the residue was dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v), and the obtained eluate was purified in slurry with isopropyl ether to obtain the entitled compound (31.0 mg, 23%) as a white solid.

Fuente