Reacción #45647

Ecuación de reacción

ethyl acetate

triethylamine

(3S)-3-(dimethylamino)pyrrolidine

7-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

Rendimiento 93.3%

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

Rendimiento 93.3%

Disolventes

brine

dimethyl sulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   OtroThe aqueous layer was separated
3. 3
   Extracciónthis was extracted twice with ethyl acetate
4. 4
   Lavadothis was washed with saturated brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   OtroThe insoluble matter was separated by filtration
7. 7
   Otrothe solvent was evaporated away
8. 8
   Otrothe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

Procedimiento

7-Fluoro-2-(1-hydroxy-1-methylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-112) (35 mg, 0.11 mmol) was dissolved in anhydrous dimethyl sulfoxide (2 ml), and at room temperature, triethylamine (24 μl, 0.17 mmol) and (3S)-3-(dimethylamino)pyrrolidine (22 μl, 0.17 mmol) were added. This mixture liquid was stirred at 90° C. for 12 hours, then cooled to room temperature. This was fractionated with ethyl acetate and saturated brine. The aqueous layer was separated, and this was extracted twice with ethyl acetate. The organic layers were combined, this was washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (41.5 mg, 91%) as a white solid. This was further recrystallized from hexane/diethyl ether to obtain a cream powder (27.5 mg).

Fuente