2-[2-(2,2-Difluoroethyl)guanidino]-4-[(2-aminoethyl)-thiomethyl]thiazole → HCID 178485062, compound

HRID 364319Notes

Reaction equation

HRID 364319 reaction equation
[F:1][CH:2]([F:18])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH2:16])[N:11]=1>C(O)C>[F:18][CH:2]([F:1])[CH2:3][N:4]=[C:5]([NH2:17])[NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH:16][C:7]([NH:11][CH3:10])=[N:6][C:5]#[N:4])[N:11]=1

Participants

3

Reactant 1

HCID 212987452-[2-(2,2-Difluoroethyl)guanidino]-4-[(2-aminoethyl)-thiomethyl]thiazole

Product 1

HCID 178485062HCID 178485062, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dimethyl (cyanoimido)dithiocarbonate (0.07 g.) and 2-[2-(2,2-difluoroethyl)guanidino]-4-[(2-aminoethyl)thiomethyl]thiazole (0.15 g.) were dissolved in ethanol (3 ml.) and heated under reflux for 20 minutes. The solvent was evaporated and the residual gum was dissolved in ethanolic methylamine (33% w/v, 3 ml.) and allowed to stand at room temperature for 16 hours. The solvent was evaporated and the residual gum purified by preparative thin layer chromatography using ethyl acetate/methanol/ammonia 6:1:1 v/v/v as developing solvent. The appropriate zone of the chromatogram was isolated and extracted with methanol/ammonia 10:1 v/v. The solvent was evaporated and the residue was dissolved in ethyl acetate, filtered and added to a solution of maleic acid (0.1 g.) in ethyl acetate. The precipitate was filtered to give 2-[2-(2,2-difluoroethyl)guanidino]-4-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]thiazole (0.11 g.), m.p. 108°-112° (decomp.) containing 1.25 molar equivalents of maleic acid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 minutes
  3. customThe solvent was evaporated
  4. dissolutionthe residual gum was dissolved in ethanolic methylamine (33% w/v, 3 ml.)
  5. customThe solvent was evaporated
  6. customthe residual gum purified by preparative thin layer chromatography
  7. customThe appropriate zone of the chromatogram was isolated
  8. extractionextracted with methanol/ammonia 10:1 v/v
  9. customThe solvent was evaporated
  10. dissolutionthe residue was dissolved in ethyl acetate
  11. filtrationfiltered
  12. additionadded to a solution of maleic acid (0.1 g.) in ethyl acetate
  13. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-f1a16f59e28c4e76b400df0a57aab143
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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