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2-Pyrazinecarboxylic acid → 4-[3-(2-Pyrazinecarbonylamino)propylthio]pyridine

HRID 6163
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 6163
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.ON1C(=O)CCC1=O.Cl.C(N=C=NCCCN(C)C)C.Cl.Cl.[NH2:32][CH2:33][CH2:34][CH2:35][S:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([NH:32][CH2:33][CH2:34][CH2:35][S:36][C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1)=[O:9]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10472-Pyrazinecarboxylic acidHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 190792594-(3-Aminopropylthio)pyridine dihydrochloride

Produkt 1

HCID 152315024-[3-(2-Pyrazinecarbonylamino)propylthio]pyridineAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g (8.06 mmol) of 2-pyrazinecarboxylic acid and 1.21 g (10.5 mmol) of N-hydroxysuccinimide in 70 ml of methylene-chloride, 1.85 g (9.67 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 1 hour. Further, 1.94 g (8.06 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was washed with saturated aqueous sodium bicarbonate and water, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 0.751 g of the desired compound (34.0% yield, colorless powder).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. stirringthe mixture was stirred at room temperature for 3 hours
  4. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate and water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d55965f78437450f9aef72b94ae9f168
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05246948

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