Ethyl orthoformate → HCID 69192155, Verbindung

HRID 1187398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187398
[CH:1](OCC)(OCC)OCC.Cl.N1C=CC=CC=1.[C:18]([O:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][N:34]=2)[N:29]=[CH:28][C:27]=1[NH2:36])(=[O:20])[CH3:19]>C1(C)C=CC=CC=1.ClCCl>[C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26]2[C:35]3[N:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N:29]=[CH:28][C:27]=2[N:36]=[CH:1]1)(=[O:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 31214Ethyl orthoformate2×HCID 10176127Pyridinium chlorideHCID 68539256HCID 68539256, Verbindung

Produkt 1

HCID 69192155HCID 69192155, VerbindungAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethyl orthoformate (1.86 mL, 17.0 mmol) and pyridine hydrochloride (0.164 g, 1.42 mrnmol) were added to a stirred suspension of 3-[(3-amino[1,5]naphthyridin-4-yl)amino]propyl acetate (prepared as described in Part C of Examples 127-135, 3.70 g, 14.2 mmol) in toluene (70 mL). The mixture was heated at reflux with a Dean-Stark trap. After 2.5 hours, additional triethyl orthoformate (1 mL) was added and heating was continued for another 2 hours. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure to afford a dark oil that was dissolved in dichloromethane (100 mL). The solution was washed with saturated aqueous sodium bicarbonate (50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 3.50 g of 3-(1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)propyl acetate as an orange oil that was used without further purification in the next step.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux with a Dean-Stark trap
  3. temperatureheating
  4. waitwas continued for another 2 hours
  5. concentrationwas concentrated under reduced pressure
  6. customto afford a dark oil that
  7. washThe solution was washed with saturated aqueous sodium bicarbonate (50 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-665b643b3cdb4fbaaa43d69673013a53
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673932B2

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