Cysteamine Hydrochloride → 2-[2-(2,2,2-Trifluoroethyl)guanidino]-6-[(2-aminoethyl)-thio]pyrazine

HRID 1902325Notes

Reaction equation

HRID 1902325 reaction equation
[H-].[Na+].Cl.[NH2:4][CH2:5][CH2:6][SH:7].[F:8][C:9]([F:23])([F:22])[CH2:10][N:11]=[C:12]([NH2:21])[NH:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=1>C(O)C>[F:8][C:9]([F:23])([F:22])[CH2:10][N:11]=[C:12]([NH2:21])[NH:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16]([S:7][CH2:6][CH2:5][NH2:4])[N:15]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 24758Sodium hydrideHCID 212987082-(2,2,2-Trifluoroethyl)guanidino-6-chloropyrazine

Product 1

HCID 212987512-[2-(2,2,2-Trifluoroethyl)guanidino]-6-[(2-aminoethyl)-thio]pyrazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydride (50% w/w dispersion in oil; 0.114 g.) was added portionwise to ethanol (2 ml.). To the resulting solution was added 2-aminoethanethiol hydrochloride (0.134 g.) and the mixture stirred at room temperature. 2-[2-(2,2,2-Trifluoroethyl)guanidino]-6-chloropyrazine (0.1 g.) was added and the mixture heated under reflux on a steam bath for 22 hours. The mixture was cooled, evaporated, water added and extracted with ethyl acetate. The extracts were dried over magnesium sulphate, filtered and the filtrate evaporated to yield 2-[2-(2,2,2-trifluoroethyl)guanidino]-6-[(2-aminoethyl)-thio]pyrazine as a gum (0.16 g.) which was used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux on a steam bath for 22 hours
  3. temperatureThe mixture was cooled
  4. customevaporated
  5. additionwater added
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extracts were dried over magnesium sulphate
  8. filtrationfiltered
  9. customthe filtrate evaporated

Sources & evidence

ORD record
ord-ea01dbcd665d4f87ba90f58384d5d5b6
Source dataset
uspto-grants-1982_12
Patent number
US04362728

Reaction notes

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