Sodium hydride → 2-[2-(2,2,2-Trifluoroethyl)guanidino]-6-(3-aminopropylthio)pyrazine

HRID 364325

Reaktionsgleichung

Reaktionsgleichung von HRID 364325
[H-].[Na+].Cl.[NH2:4][CH2:5][CH2:6][CH2:7][SH:8].[F:9][C:10]([F:24])([F:23])[CH2:11][N:12]=[C:13]([NH2:22])[NH:14][C:15]1[CH:20]=[N:19][CH:18]=[C:17](Cl)[N:16]=1>C(O)C>[F:24][C:10]([F:9])([F:23])[CH2:11][N:12]=[C:13]([NH2:22])[NH:14][C:15]1[CH:20]=[N:19][CH:18]=[C:17]([S:8][CH2:7][CH2:6][CH2:5][NH2:4])[N:16]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 197870(3-Mercaptopropyl)ammonium chlorideHCID 212987082-(2,2,2-Trifluoroethyl)guanidino-6-chloropyrazine

Produkt 1

HCID 212988192-[2-(2,2,2-Trifluoroethyl)guanidino]-6-(3-aminopropylthio)pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium hydride (50% w/w dispersion in oil; 0.57 g.) was added to ethanol (10 ml.) portionwise. To the resulting solution was added 3-aminopropanethiol hydrochloride (0.75 g.) and the mixture stirred at room temperature. 2-[2-(2,2,2-Trifluoroethyl)guanidino-6-chloropyrazine (0.5 g.) was added in one portion and the mixture heated under reflux on the steam bath overnight. The mixture was cooled, evaporated, water (10 ml.) added and the mixture extracted with ethyl acetate. The extracts were dried over magnesium sulphate, filtered and evaporated to yield an oil, which was chromatographed eluting with methanol/methylene chloride/ammonia 10:40:1 v/v/v to yield 2-[2-(2,2,2-trifluoroethyl)guanidino]-6-(3-aminopropylthio)pyrazine as a pale yellow solid (0.39 g.) which was used without further purification.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureunder reflux on the steam bath overnight
  3. temperatureThe mixture was cooled
  4. customevaporated
  5. additionwater (10 ml.) added
  6. extractionthe mixture extracted with ethyl acetate
  7. dry with materialThe extracts were dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customto yield an oil, which
  11. customwas chromatographed
  12. washeluting with methanol/methylene chloride/ammonia 10:40:1 v/v/v

Quellen und Nachweise

ORD-Eintrag
ord-51c0ba1bbd7d4ac39c54a10b6adb3b5b
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604465

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