Methyl chloroformate → 5-[2-(Methoxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine

HRID 5483

Reaction equation

HRID 5483 reaction equation
[NH2:1][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.Cl[C:22]([O:24][CH3:25])=[O:23]>C(Cl)Cl>[CH3:25][O:24][C:22]([NH: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:23]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 98164115-[2-(Methoxycarbonylamino)ethylthio]imidazo[1,2-a]pyridineYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.93 g, 10 mmoles) and triethylamine (1.53 ml, 11 mmoles) in methylene chloride (30 ml) was added methyl chloroformate (0.77 ml, 10 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was washed in turn with aqueous sodium bicarbonate and water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography [eluent: ethanol/etyl acetate (1:10)] to obtain 1.68 g of the desired product (66.9%, colorless crystals).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 20 minutes
  3. washThe reaction mixture was washed in turn with aqueous sodium bicarbonate and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by column chromatography [eluent: ethanol/etyl acetate (1:10)]

Sources & evidence

ORD record
ord-153f77bc2a644cc5babb03217d5b3d48
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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