Methylamine → HCID 178485213, compound

HRID 34816Notes

Reaction equation

HRID 34816 reaction equation
[F:1][C:2]([F:27])([F:26])[CH2:3][N:4]=[C:5]([NH2:25])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH:16][C:17](=[N:20][S:21]([CH3:24])(=[O:23])=[O:22])SC)[N:11]=1.[CH3:28][NH2:29]>>[F:27][C:2]([F:1])([F:26])[CH2:3][N:4]=[C:5]([NH2:25])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH:16][C:17]([NH:29][CH3:28])=[N:20][S:21]([CH3:24])(=[O:22])=[O:23])[N:11]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 178504071HCID 178504071, compound

Product 1

HCID 178485213HCID 178485213, compound

Procedure

2-[2-(2,2,2-Trifluoroethyl)guanidino]-4-[2-(3-methylsulphonyl-2-methylisothioureido)ethylthiomethyl]thiazole (0.4 g.) was dissolved in ethanolic methylamine (33% w/v 15 ml.) and allowed to stand at room temperature for 64 hours. The solvent was evaporated and the residual gum was purified by preparative thin layer chromatography using chloroform/methanol/ammonia 8:2:0.2 v/v/v as developing solvent. The appropriate zone of the chromatogram was isolated and extracted with methanol/ammonia 10:1 v/v (50 ml.). The solvent was evaporated and the residual gum was dissolved in acetonitrile, filtered and the filtrate evaporated. The residual gum was dissolved in methanol and treated with a solution of excess fumaric acid in methanol. The solvent was evaporated and the residue triturated with acetonitrile to give 2-[2-(2,2,2-trifluoroethyl)guanidino]-4-[2-(2-methylsulphonyl-3-methylguanidino)ethylthiomethyl]thiazole as a cream solid (0.29 g.), m.p. 118°-123° (decomp.), containing 1.5 molar equivalents of fumaric acid.

Workup

  1. customThe solvent was evaporated
  2. customthe residual gum was purified by preparative thin layer chromatography
  3. customThe appropriate zone of the chromatogram was isolated
  4. extractionextracted with methanol/ammonia 10:1 v/v (50 ml.)
  5. customThe solvent was evaporated
  6. dissolutionthe residual gum was dissolved in acetonitrile
  7. filtrationfiltered
  8. customthe filtrate evaporated
  9. dissolutionThe residual gum was dissolved in methanol
  10. additiontreated with a solution of excess fumaric acid in methanol
  11. customThe solvent was evaporated
  12. customthe residue triturated with acetonitrile

Sources & evidence

ORD record
ord-6778e57e14f842bda061332667de0836
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

Loading…