Ethyl orthoformate → 6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline

HRID 432702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432702
[CH:1](OCC)(OCC)OCC.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]3[N:34]=[N:35][N:36]=[C:26]3[C:25]=2[NH2:37])[CH:12]=1>ClCCCl.C(=O)(O)[O-].[Na+]>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][N:23]2[C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]4[N:34]=[N:35][N:36]=[C:26]4[C:25]=3[N:37]=[CH:1]2)[CH:12]=1

Komponenten

5

Edukt 2

HCID 31214Ethyl orthoformateHCID 18760199N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamine

Produkt 1

HCID 187601846-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinolineAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Triethyl orthoformate (21.1 ml, 127 mmol) was added to a solution of N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamine (30.8 g, 84.7 mmol) in 1,2-dichloroethane (750 ml) and the reaction was heated to reflux for 3 hours. The reaction was cooled to room temperature and diluted with saturated sodium bicarbonate (200 ml). The phases were separated and the aqueous layer was extracted with dichloromethane (3×75 ml). The combined organic fractions were washed with brine (200 ml), dried (Na2SO4) and concentrated to provide an orange solid. The solid was triturated with diethyl ether and then filtered to yield 28.7 g of 6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline as a tan/orange solid.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×75 ml)
  5. washThe combined organic fractions were washed with brine (200 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto provide an orange solid
  9. customThe solid was triturated with diethyl ether
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-0f0e109acde2476cbde5846b8ca307b1
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664260B2

Notizen zur Reaktion

Wird geladen…