3-Amino-1-propanol → 5-[2-[3-(Hydroxy)propylcarbamoyloxy]ethylthio]imdazo[1,2-a]pyridine

HRID 5447

Reaktionsgleichung

Reaktionsgleichung von HRID 5447
O([C:8]([O:10][CH2:11][CH2:12][S:13][C:14]1[N:19]2[CH:20]=[CH:21][N:22]=[C:18]2[CH:17]=[CH:16][CH:15]=1)=[O:9])C1C=CC=CC=1.[NH2:23][CH2:24][CH2:25][CH2:26][OH:27]>C(Cl)(Cl)Cl>[OH:27][CH2:26][CH2:25][CH2:24][NH:23][C:8]([O:10][CH2:11][CH2:12][S:13][C:14]1[N:19]2[CH:20]=[CH:21][N:22]=[C:18]2[CH:17]=[CH:16][CH:15]=1)=[O:9]

Komponenten

4

Edukt 2

HCID 90863-Amino-1-propanolHCID 233628305-[2-(Phenoxycarbonyloxy)ethylthio]imidazo[1,2-a]pyridine

Produkt 1

HCID 233628315-[2-[3-(Hydroxy)propylcarbamoyloxy]ethylthio]imdazo[1,2-a]pyridineAusbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. washwhich was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThen, the residue was purified by column chromatography (eluent: methanol/chloroform=1:20)

Quellen und Nachweise

ORD-Eintrag
ord-349268ab472d46378b63207ed9f22d8d
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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