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

HRID 381345

Reaktionsgleichung

Reaktionsgleichung von HRID 381345
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[N+:28]([C:31]1[C:32]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[N:33][CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:6]=[CH:7][C:8]([C:11]([N:40]2[CH2:41][CH2:42][N:37]([C:32]3[C:31]([N+:28]([O-:30])=[O:29])=[CH:36][CH:35]=[CH:34][N:33]=3)[CH2:38][CH2:39]2)=[O:13])=[N:9][CH:10]=1

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 37788341-(3-Nitropyridin-2-yl)piperazine

Produkt 1

HCID 108616096-[1-(3-Nitro-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid methyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

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%).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. customthe mixture was reacted at 5° C.˜10° C. for 2 hours
  3. washThe reaction mixture was washed with aqueous sodium bicarbonate and water each twice and then, the separated organic layer
  4. concentrationwas concentrated under reduced pressure
  5. additionThe concentrated residue was treated with ethanol for crystallization and water
  6. additionwas added
  7. filtrationthe precipitate was filtered
  8. customThe crude product was recrystallized with ethanol and ether
  9. filtrationfiltered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-804b4d70de9f4408a13d6d9c560f0edb
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306860B1

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