2-[2-(2,2,2-Trifluoroethyl)guanidino]-6-(2-aminoethylthiomethyl)pyridine → HCID 178485058, compound

HRID 34784Notes

Reaction equation

HRID 34784 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][S:14][CH2:15][CH2:16][NH2:17])[N:8]=1>C(#N)C>[F:20][C:2]([F:1])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][S:14][CH2:15][CH2:16][NH:17][C:7]([NH:8][CH3:9])=[N:6][C:5]#[N:4])[N:8]=1

Participants

3

Reactant 1

HCID 212988302-[2-(2,2,2-Trifluoroethyl)guanidino]-6-(2-aminoethylthiomethyl)pyridine

Product 1

HCID 178485058HCID 178485058, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dimethyl(cyanoimido)dithiocarbonate (0.12 g.) was added to a solution of 2-[2-(2,2,2-trifluoroethyl)guanidino]-6-(2-aminoethylthiomethyl)pyridine (0.23 g.) in acetonitrile (5 ml.) and the solution left at room temperature for 18 hours and then evaporated to dryness. The residue was dissolved in 33% w/v methylamine in ethanol (5 ml.) and the solution left at room temperature for 18 hours and then evaporated to dryness. The residue was purified by preparative thin layer chromatography using ethyl acetate/methanol/ammonia 6:1:0.5 v/v/v as the developing solvent to give 2-[2-(2,2,2-trifluoroethyl)guanidino]-6-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]pyridine (0.12 g.) characterised as the hydrogen maleate, m.p. 137°-140° after recrystallisation from acetone.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in 33%
  3. waitthe solution left at room temperature for 18 hours
  4. customevaporated to dryness
  5. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-ac006d0d51654bca93a7951270324125
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

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