Triethylamine → 5-[2-(Methylcarbamoyloxy)ethylthio]imidazo[1,2-a]pyridine

HRID 5446Notes

Reaction equation

HRID 5446 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:21][N:22]=[C:23]=[O:24]>C(Cl)Cl>[CH3:21][NH:22][C:23]([O:1][CH2:2][CH2:3][S:4][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 144568495-[2-(Hydroxy)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628175-[2-(Methylcarbamoyloxy)ethylthio]imidazo[1,2-a]pyridineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(hydroxy)ethylthio]imidazo[1,2-a]pyridine (971 mg, 5 mmoles) and trietylamine (0.91 ml, 6.53 mmoles) in methylene chloride (40 ml) was added methyl isocyanate (0.65 ml, 11 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 12 hours. The reaction mixture was washed with saturated saline and dried over anhydrous magnesium sulfater. After the solvent was distilled off, the residue was purified by column chromatography (eluent: methanol/chloroform=1:20) to obtain 1.07 g of the desired product (85.2%, colorless crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. washThe reaction mixture was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfater
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: methanol/chloroform=1:20)

Sources & evidence

ORD record
ord-38cd054a169a4254b93577d431c563a5
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

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