Réaction #468527

Équation de réaction

5-(Methoxycarbonyl)-2-pyridinecarboxylic acid

triethylamine

1-(3-Nitro-2-pyridyl)piperazine

triethylamine

pivaloyl chloride

→

desired compound

Rendement 86.0%

6-[1-(3-nitro-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid methyl ester

Rendement 86.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled
2. 2
   Autrethe mixture was reacted at 5° C.˜10° C. for 2 hours
3. 3
   LavageThe reaction mixture was washed with aqueous sodium bicarbonate and water each twice and then, the separated organic layer
4. 4
   Concentrationwas concentrated under reduced pressure
5. 5
   workup.ADDITIONThe concentrated residue was treated with ethanol for crystallization and water
6. 6
   workup.ADDITIONwas added
7. 7
   Filtrationthe precipitate was filtered
8. 8
   AutreThe crude product was recrystallized with ethanol and ether
9. 9
   Filtrationfiltered
10. 10
    Autredried

Mode opératoire

5-(Methoxycarbonyl)-2-pyridinecarboxylic acid (20 g) was added in methylene chloride (200 ml), and then, dissolved with the addition of triethylamine (17 ml). The mixture was cooled, pivaloyl chloride (14.5 ml) was added at 0° C.˜5° C. and stirred at 5° C. for 2 hours. 1-(3-Nitro-2-pyridyl)piperazine (23 g) and triethylamine (18 ml) were added to the solution in order and the mixture was reacted at 5° C.˜10° C. for 2 hours. The reaction mixture was washed with aqueous sodium bicarbonate and water each twice and then, the separated organic layer was concentrated under reduced pressure. The concentrated residue was treated with ethanol for crystallization and water was added, then the precipitate was filtered. The crude product was recrystallized with ethanol and ether, filtered and dried to give a desired compound of 35.3 g (yield: 86%).

Source