Triethylamine → Ethanamine,2-(imidazo[1,2-a]pyridin-5-ylthio)-n-methyl-

HRID 5433

Reaction equation

HRID 5433 reaction equation
CS(O[CH2:6][CH2:7][S:8][C:9]1[N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1)(=O)=O.[CH2:18]([N:20](CC)CC)C.CN.CO>C(Cl)(Cl)Cl>[CH3:18][NH:20][CH2:6][CH2:7][S:8][C:9]1[N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 233629605-[2-(Methylsulfonyloxy)ethylthio]imidazo[1,2-a]pyridineHCID 57454252Monomethylamine methanol

Product 1

HCID 23362988Ethanamine,2-(imidazo[1,2-a]pyridin-5-ylthio)-n-methyl-Yield 47.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-[2-(methylsulfonyloxy)ethylthio]imidazo[1,2-a]pyridine (2.18 g, 8 mmoles), triethylamine (2.24 ml, 16 mmoles) and a 40% methylamine-methanol solution (20 ml) in chloroform (20 ml) was heated at reflux for 3 hours. The reaction solution was washed with an aqueous 3N-sodium hydroxide solution and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: methanol/chloroform=1:10) to obtain 781 mg of the desired product (47.1%, light brown oily product).

Workup

  1. temperatureat reflux for 3 hours
  2. washThe reaction solution was washed with an aqueous 3N-sodium hydroxide solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography (eluent: methanol/chloroform=1:10)

Sources & evidence

ORD record
ord-824f8a15b5d240dc96f33facfa1f2b99
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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