Formaldehyde → 5-[2-(Methylsulfonylamino)ethylthio]3-morpholinomethylimidazo[1,2-a]pyridine

HRID 1081712

반응식

HRID 1081712 반응식
[CH2:1]=O.[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH3:9][S:10]([NH:13][CH2:14][CH2:15][S:16][C:17]1[N:22]2[CH:23]=[CH:24][N:25]=[C:21]2[CH:20]=[CH:19][CH:18]=1)(=[O:12])=[O:11]>C(O)(=O)C>[CH3:9][S:10]([NH:13][CH2:14][CH2:15][S:16][C:17]1[N:22]2[C:23]([CH2:1][N:3]3[CH2:8][CH2:7][O:6][CH2:5][CH2:4]3)=[CH:24][N:25]=[C:21]2[CH:20]=[CH:19][CH:18]=1)(=[O:12])=[O:11]

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 152293635-[2-(Methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridine

생성물 1

HCID 233628515-[2-(Methylsulfonylamino)ethylthio]3-morpholinomethylimidazo[1,2-a]pyridine수율 71.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of 37% formalin (178 mg, 2.2 mmoles) in acetic acid (2 ml) was added morpholin (192 μl, 2.2 mmoles) under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. 5-[2-(methylsulfonylamino)ethylthio]imidazo[1,2-a]pyridine (543 mg, 2 mmoles) was added to the reaction mixture, followed by stirring at 60° C. for 2 hours. After the solvent was distilled off, the residue was dissolved in chloroform (50 ml) and washed with 1N NaOH (10 ml). Then, the aqueous layer was extracted with chloroform (30 ml×3) and the combined chloroform layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10→1:5) to obtain 530 mg of the desired product (71.5%, colorless solid).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. stirringby stirring at 60° C. for 2 hours
  4. distillationAfter the solvent was distilled off
  5. dissolutionthe residue was dissolved in chloroform (50 ml)
  6. washwashed with 1N NaOH (10 ml)
  7. extractionThen, the aqueous layer was extracted with chloroform (30 ml×3)
  8. dry with materialthe combined chloroform layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10→1:5)

출처 및 근거

ORD 기록
ord-e05830de9ec74d43a4d9eff74eb3a55f
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05587383

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