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

HRID 1081726

반응식

HRID 1081726 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1c05986e8943460fbfcf26be8e32b5fa
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05587383

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