Ethanol → 7-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

HRID 244809

Reaktionsgleichung

Reaktionsgleichung von HRID 244809
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:21]([O:23][CH2:24][C:25](Cl)=O)[CH3:22].C(O)C>C(#N)C.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])[C:22]([CH2:21][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Komponenten

6

Edukt 3

HCID 702EthanolHCID 84189Ethoxyacetyl chlorideHCID 690787337-bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine

Produkt 1

HCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinolineAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

7-Bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine (45 g) was dissolved in acetonitrile (1.3 L) and triethylamine (19.4 mL). Ethoxyacetyl chloride (18.0 g) was added dropwise to the solution and the reaction was stirred for 16 hours. The solvent was removed under reduced pressure to afford a tan solid. The solid was added to a solution of ethanol (1 L) and triethylamine (77.5 mL) and heated at reflux for 4 hours. The solvent was removed under reduced pressure. Water was added to the solid residue and the crude product was recovered by filtration. Recrystallization from acetonitrile yielded 36.25 g of 7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline as a tan crystalline solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customto afford a tan solid
  3. temperatureheated
  4. temperatureat reflux for 4 hours
  5. customThe solvent was removed under reduced pressure
  6. additionWater was added to the solid residue
  7. filtrationthe crude product was recovered by filtration
  8. customRecrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-eb4b544c9c1842b1a3f503a487f97aa0
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658666B2

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