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

HRID 1081712

Reaktionsgleichung

Reaktionsgleichung von HRID 1081712
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 233628515-[2-(Methylsulfonylamino)ethylthio]3-morpholinomethylimidazo[1,2-a]pyridineAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e05830de9ec74d43a4d9eff74eb3a55f
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587383

Verknüpfte Notizen

Wird geladen…