5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 178483232, compound

HRID 2412563Notes

Reaction equation

HRID 2412563 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15](=[N:18][C:19]#[N:20])SC)[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH3:21][N:22]([CH2:24][C:25]1[O:29][C:28]([CH2:30][S:31][CH2:32][CH2:33][NH2:34])=[CH:27][CH:26]=1)[CH3:23]>C(#N)C>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15]([NH:34][CH2:33][CH2:32][S:31][CH2:30][C:28]2[O:29][C:25]([CH2:24][N:22]([CH3:23])[CH3:21])=[CH:26][CH:27]=2)=[N:18][C:19]#[N:20])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine2×HCID 178503927HCID 178503927, compound

Product 1

HCID 178483232HCID 178483232, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-guanidino-4-[2-(3-cyano-2-methylisothioureido)ethylthiomethyl]thiazole (0.5 g) and 2-[5-dimethylaminomethylfuran-2-ylmethylthio]ethylamine (0.33 g) in acetonitrile (10 ml) was heated under reflux for 48 hours. A further portion of 2-[5-dimethylaminomethylfuran-2-ylmethylthio]ethylamine (0.5 g) was added and the mixture was heated under reflux for 16 hours. The mixture was evaporated to dryness and the residue was partitioned between water and ethyl acetate. The ethyl acetate layer was dried with anhydrous magnesium sulphate and evaporated. The residual gum was triturated four times with warm diethyl ether (10 ml). The residue was further purified by applying to Merck 60 F254 preparative plates and eluting with acetonitrile/ammonia (s.g. 0.880) 7:1 v/v. The product was redissolved in acetonitrile (5 ml), and the solution filtered and evaporated to give 2-guanidino-4-[2-(2-cyano-3-[2-(5-dimethylaminomethylfuran-2-ylmethylthio)ethyl]guanidino)-ethylthiomethyl]thiazole as pale brown gum (0.15 g).

Workup

  1. temperatureunder reflux for 48 hours
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 16 hours
  4. customThe mixture was evaporated to dryness
  5. customthe residue was partitioned between water and ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried with anhydrous magnesium sulphate
  7. customevaporated
  8. customThe residual gum was triturated four times with warm diethyl ether (10 ml)
  9. customThe residue was further purified
  10. washeluting with acetonitrile/ammonia (s.g. 0.880) 7:1 v/v
  11. dissolutionThe product was redissolved in acetonitrile (5 ml)
  12. filtrationthe solution filtered
  13. customevaporated

Sources & evidence

ORD record
ord-3bfe64124a0f416da28d2f795cd14980
Source dataset
uspto-grants-1985_01
Patent number
US04493840

Reaction notes

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