Reacción #45696

Ecuación de reacción

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile

diisopropylethylamine

3-hydroxy-1-azetidine hydrochloride

→

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

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby heating
2. 2
   Temperaturaunder reflux in a sealed tube under nitrogen atmosphere for 6 hours
3. 3
   TemperaturaAfter cooling
4. 4
   Lavadodilution with methylene chloride and washing with water and saturated brine
5. 5
   Secadothe organic layer was dried over anhydrous sodium sulfate
6. 6
   Otrothe solvent was evaporated away under reduced pressure
7. 7
   OtroThe resisting residue was recrystallized
8. 8
   Otropurified with n-hexane/ethyl acetate
9. 9
   Otroto obtain the entitled compound (123 mg, quant) as a yellow white solid

Procedimiento

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (100 mg, 0.35 mmol) was dissolved in methylene chloride (2 ml), then diisopropylethylamine (237 μl, 1.39 mmol) and 3-hydroxy-1-azetidine hydrochloride (76 mg, 0.70 mmol) were added, followed by heating under reflux in a sealed tube under nitrogen atmosphere for 6 hours. After cooling, dilution with methylene chloride and washing with water and saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resisting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (123 mg, quant) as a yellow white solid.

Fuente