Thionyl Chloride → N'-[3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N,N-dimethylethane-1,2-diamine

HRID 2090241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090241
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])[N:14]([CH2:15][CH2:16][CH2:17]O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)(Cl)=O>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])[N:14]([CH2:15][CH2:16][CH2:17][NH:12][CH2:11][CH2:10][N:14]([CH3:15])[CH3:13])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 684322443-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol

Produkt 1

HCID 68432302N'-[3-(4-Amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N,N-dimethylethane-1,2-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of the product from step (v) (0.96 g) and thionyl chloride (10 mL) in DCM (20 mL) was heated under reflux for 6 h then evaporated under reduced pressure. The residue was dissolved in acetonitrile (20 mL) then N,N-dimethylethylenediamine (10 mL) added and the mixture heated under reflux for 24 h. The solvent was removed under reduced pressure and the residue purified by RPHPLC, yield 0.512 g.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. customthen evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in acetonitrile (20 mL)
  5. additionN,N-dimethylethylenediamine (10 mL) added
  6. temperaturethe mixture heated
  7. temperatureunder reflux for 24 h
  8. customThe solvent was removed under reduced pressure
  9. customthe residue purified by RPHPLC, yield 0.512 g

Quellen und Nachweise

ORD-Eintrag
ord-a6b876a359624606a34ae2bc2d260994
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436178B2

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