Réaction #7024

Équation de réaction

chloroform

5-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine

3-amino-2-methylbenzamide

D-10-camphorsulfonic acid

→

compound

Rendement 56.1%

3-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methylbenzamide

Rendement 56.1%

Solvants

1,3-dimethyl-2-imidazolidinone

Conditions de réaction

Traitement

1. 1
   TempératureAfter the reaction solution was cooled to ambient temperature
2. 2
   Lavagewas then washed with saturated aqueous sodium hydrogen carbonate solution
3. 3
   SéchageThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   Autrethe solvent was evaporated under reduced pressure
5. 5
   AutreThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Mode opératoire

5-[5-(3-Methoxypropyl)-1,3,4-oxadiazol-2-yl]-2-phenylpyridine (1.0 g) prepared in the Reference Example 7 was dissolved in 1,3-dimethyl-2-imidazolidinone (10 ml), followed by addition of 3-amino-2-methylbenzamide (1.53 g) prepared in the Reference Example 6 and D-10-camphorsulfonic acid (290 mg), and stirred at 200° C. for 16 hours. After the reaction solution was cooled to ambient temperature, chloroform was added to the solution, which was then washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1), to afford the entitled compound (812 mg, 56%). The physico-chemical values are as follows.

Source