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

HRID 1081752Notes

Reaction equation

HRID 1081752 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-4ce6926292f84b6ba8dda1aac6ce2dde
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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