Cysteamine Hydrochloride → 5-[2-(Amino)ethylthio]-2-methylimidazo[1,2-a]pyridine

HRID 5429

Reaction equation

HRID 5429 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[H-].[Na+].Cl[C:9]1[N:14]2[CH:15]=[C:16]([CH3:18])[N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1>C(O)C>[NH2:2][CH2:3][CH2:4][S:5][C:9]1[N:14]2[CH:15]=[C:16]([CH3:18])[N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 24758Sodium hydrideHCID 139119055-Chloro-2-methylimidazo[1,2-A]pyridine

Product 1

HCID 233629245-[2-(Amino)ethylthio]-2-methylimidazo[1,2-a]pyridineYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of cysteamine hydrochloride (2.95 g, 26 mmoles) in ethanol (100 ml) was added 60% sodium hydride (oily; 2.08 g, 26 mmoles) with stirring under ice-cooling and the mixture was stirred for 5 minutes. 5-chloro-2-methylimidazo[1,2-a]pyridine (3.33 g, 20 mmoles) was added to the mixture, followed by heating at reflux for 3 hours. After the solvent was distilled off, chloroform was added to the residue which was washed with 1N-NaOH and dried over anhydrous potassium carbonate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate/ethanol/triethylamine=6:2:1) to obtain 2.2 g of the desired product (53.6%, brown oily product).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 5 minutes
  3. temperatureby heating
  4. temperatureat reflux for 3 hours
  5. distillationAfter the solvent was distilled off
  6. additionchloroform was added to the residue which
  7. washwas washed with 1N-NaOH
  8. dry with materialdried over anhydrous potassium carbonate
  9. distillationAfter the solvent was distilled off
  10. customthe residue was purified by column chromatography (eluent: ethyl acetate/ethanol/triethylamine=6:2:1)

Sources & evidence

ORD record
ord-56786f33a9bf4fdaa5b52ea804ea60fd
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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