Reaktion #5543

ord-349268ab472d46378b63207ed9f22d8d

Reaktionsgleichung

O=C(OCCSc1cccc2nccn12)Oc1ccccc1
5-[2-(phenoxycarbonyloxy)ethylthio]imidazo[1,2-a]pyridine
NCCCO
3-aminopropanol
O=C(NCCCO)OCCSc1cccc2nccn12
desired product
Ausbeute 55.6%
O=C(NCCCO)OCCSc1cccc2nccn12
5-[2-[3-(hydroxy)propylcarbamoyloxy]ethylthio]imdazo[1,2-a]pyridine
Ausbeute 55.6%

Lösungsmittel

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction mixture was cooled
  2. 2
    Waschenwhich was washed with water
  3. 3
    Trocknendried over anhydrous magnesium sulfate
  4. 4
    workup.DISTILLATIONthe solvent was distilled off
  5. 5
    SonstigeThen, the residue was purified by column chromatography (eluent: methanol/chloroform=1:20)

Vorschrift

To 5-[2-(phenoxycarbonyloxy)ethylthio]imidazo[1,2-a]pyridine (1.10 g, 3.50 mmoles) was added 3-aminopropanol (0.27 ml, 3.52 mmoles) and the mixture was stirred at 120° C. for 1.5 hours. The reaction mixture was cooled by standing and chloroform was added thereto, which was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. Then, the residue was purified by column chromatography (eluent: methanol/chloroform=1:20) to obtain 575 mg of the desired product (55.6%, colorless crystals).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05244908uspto-grants-1993_09