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

HRID 1608635Notes

Reaction equation

HRID 1608635 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)etylthio]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 mixture was washed with 3N NaOH 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 mixture was washed with 3N NaOH
  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-68f7bd5c0d304e5794f71a2aa322b088
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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