Ammonia → 2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 606045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606045
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:22][O:23][CH2:24][CH3:25])[N:14]([CH2:15][C:16]3[O:20][N:19]=[C:18]([CH3:21])[CH:17]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:26]>CO>[CH2:24]([O:23][CH2:22][C:13]1[N:14]([CH2:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[CH:17]=2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:26])[C:11]=2[N:12]=1)[CH3:25]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 866168734-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline

Produkt 1

HCID 590266862-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A slurry of 4-chloro-2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinoline (4.21 g, 11.8 mmol) in a solution of 7 M ammonia in methanol (50 mL) was heated at 150° C. for 22 hours in a Parr pressure vessel. The volatiles were removed under reduced pressure and the resulting solid was triturated with water. A tan solid was isolated and purified by flash chromatography (silica gel, gradient elution from 9:1 to 1:1 chloroform/CMA) to yield 43.2 mg of pure 2-(ethoxymethyl)-1-[(3-methylisoxazol-5-yl)methyl]-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 178.0-180.0° C.

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting solid was triturated with water
  3. customA tan solid was isolated
  4. custompurified by flash chromatography (silica gel, gradient elution from 9:1 to 1:1 chloroform/CMA)

Quellen und Nachweise

ORD-Eintrag
ord-b5685879c0d4441c93c32bfd5b0be417
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915281B2

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