三乙胺 → 5-[2-[2-(Hydroxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridine

HRID 5455

反应方程式

HRID 5455 反应方程式
[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.C([C:24]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:25]1[C:26](Cl)=[O:27])(=O)C>C(Cl)Cl>[OH:33][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([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:27]

参与物

5

反应物 3

HCID 8471三乙胺HCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridineHCID 573615642-Acetylsalicyloyl chloride

产物 1

HCID 233629775-[2-[2-(Hydroxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridine收率 56%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (3.87 g, 20 mmoles) and triethylamine (5.58 ml, 40 mmoles) in methylene chloride (200 ml) was added o-acetylsalicyloyl chloride (4.77 g, 24 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. After the solvent was distilled off, ethanol (60 ml) and 1N NaOH (40 ml) were added to the residue, followed by stirring for 1 hour. 1N HCl (40 ml) was added and ethanol was distilled off, and then the residue was extracted with chloroform and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to obtain 3.51 g of the desired product (56.0%, colorless solid).

后处理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. distillationAfter the solvent was distilled off
  4. additionethanol (60 ml) and 1N NaOH (40 ml) were added to the residue
  5. stirringby stirring for 1 hour
  6. addition1N HCl (40 ml) was added
  7. distillationethanol was distilled off
  8. extractionthe residue was extracted with chloroform
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationAfter the solvent was distilled off
  11. customthe residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

来源与证据

ORD记录
ord-d34a489740ed4a9e8f386753fe5c41ad
来源数据集
uspto-grants-1993_09
专利号
US05244908

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