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

HRID 1081726

反応式

HRID 1081726 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (3.87 g, 20 mmoles) and triethylamine (5.58 ml, 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 strirring 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).

後処理

  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. addition1N HCl (40 ml) was added
  6. distillationethanol was distilled off
  7. extractionthe residue was extracted with chloroform
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationAfter the solvent was distilled off
  10. customthe residue was purified by column chromatography (eluent:ethyl acetate/ethanol=10:1)

出典と根拠

ORDレコード
ord-1c05986e8943460fbfcf26be8e32b5fa
出典データセット
uspto-grants-1996_12
特許番号
US05587383

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