Water → HCID 21936597, Verbindung

HRID 1241675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241675
[CH2:1]([C:3]1[N:4]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N+:8]([O-])=[CH:7][C:6]=2[N:16]=1)[CH3:2].[NH4+:30].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl>[NH2:30][C:7]1[C:6]2[N:16]=[C:3]([CH2:1][CH3:2])[N:4]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:5]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 21936601HCID 21936601, Verbindung

Produkt 1

HCID 21936597HCID 21936597, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of tert-butyl 2-[2-(2-ethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate (14.3 g, 35.8 mmol) in 90 mL of CH2Cl2 was treated with 90 mL of concentrated NH4OH solution. The mixture was chilled in an ice water bath. To the rapidly stirred mixture was added solid p-toluenesulfonyl chloride (7.05 g, 37.0 mmol) over a 10 min period. The reaction mixture was then warmed to room temperature. After 30 min, the reaction was treated with 90 mL of CH2Cl2 and 90 mL of water. The organic portion was then washed with 1% Na2CO3 solution (2×), water, brine, dried over Na2SO4 and concentrated. The resulting solid was triturated in ether and filtered to yield 9.35 g of tert-butyl 2-[2-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethylcarbamate as a light tan solid.

Aufarbeitung

  1. temperatureThe mixture was chilled in an ice water bath
  2. washThe organic portion was then washed with 1% Na2CO3 solution (2×), water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting solid was triturated in ether
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-4a5313986352481ba964a4ad08bb6aaf
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115622B2

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