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Ethanolamine → 6-[4-(3-amino-2-pyridyl)piperazine-1-carbonyl]-N-(2-hydroxyethyl)pyridine-3-carboxamide

HRID 381362
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 381362
[NH2:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH2:50]([CH2:52][NH2:53])[OH:51]>C(Cl)Cl.O1CCCC1>[NH2:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20](=[O:21])[NH:53][CH2:52][CH2:50][OH:51])=[CH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 700EthanolamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 183627906-[1-(3-Amino-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid

Produkt 1

HCID 4997296-[4-(3-amino-2-pyridyl)piperazine-1-carbonyl]-N-(2-hydroxyethyl)pyridine-3-carboxamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-[1-(3-Amino-2-pyridyl)piperazine-4-yl-carbonyl]nicotinic acid (0.5 g) was added to a co-solvent of tetrahydrofuran (10 ml) and methylene chloride (10 ml) and with the successive addition of 1,3-dicyclohexylcarbodimide (0.65 g) and 1-hydroxybenzotriazole (0.23 g) at 15˜20° C., the mixture was stirred for 2 hours. With the addition of ethanolamine (0.18 ml), the mixture was stirred again at 20˜25° C. for 2 hours. Methylene chloride (30 ml) was added again to the mixture, washed with water 3 times, dried over magnesium sulfate and concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization. The solid was recrystallized with ethanol and hexane to give a desired compound of 0.44 g (yield: 78%).

Aufarbeitung

  1. stirringthe mixture was stirred again at 20˜25° C. for 2 hours
  2. washwashed with water 3 times
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionThe concentrated residue was treated with ether for crystallization
  6. customThe solid was recrystallized with ethanol and hexane

Quellen und Nachweise

ORD-Eintrag
ord-231f87ab9010466d802dbba06279a088
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06306860B1

Notizen zur Reaktion

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