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

HRID 1902327

반응식

HRID 1902327 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-61af6b0cb2a1404ab95b97a313547a58
출처 데이터셋
uspto-grants-1982_12
특허 번호
US04362728

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