Réaction #45696

Équation de réaction

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

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températureby heating
2. 2
   Températureunder reflux in a sealed tube under nitrogen atmosphere for 6 hours
3. 3
   TempératureAfter cooling
4. 4
   Lavagedilution with methylene chloride and washing with water and saturated brine
5. 5
   Séchagethe organic layer was dried over anhydrous sodium sulfate
6. 6
   Autrethe solvent was evaporated away under reduced pressure
7. 7
   AutreThe resisting residue was recrystallized
8. 8
   Autrepurified with n-hexane/ethyl acetate
9. 9
   Autreto obtain the entitled compound (123 mg, quant) as a yellow white solid

Mode opératoire

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.

Source