1,1,1-Trimethoxybutane → 1-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 9447

Reaktionsgleichung

Reaktionsgleichung von HRID 9447
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:28]=1[NH:29][CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])=[CH:26][CH:25]=[C:24]([Br:35])[CH:23]=2>C1(C)C=CC=CC=1>[Br:35][C:24]1[CH:25]=[CH:26][C:27]2[C:28]3[N:29]([CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])[C:1]([CH2:2][CH2:3][CH3:4])=[N:18][C:19]=3[CH:20]=[N:21][C:22]=2[CH:23]=1

Komponenten

5

Edukt 3

HCID 1235121,1,1-TrimethoxybutaneHCID 10176127Pyridinium chlorideHCID 219844571-(3-Amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol

Produkt 1

HCID 219841831-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-olAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Trimethyl orthobutyrate (11.61 mL, 72.6 mmol) and catalytic pyridine hydrochloride were added to a solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (22.51 g, 72.6 mmol) in anhydrous toluene (120 mL), and the reaction was heated at reflux for two hours. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was removed under reduced pressure until a precipitate began to form. Hexanes were added, and the precipitate was isolated by filtration to provide 20.17 g of 1-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureat reflux for two hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water
  6. customThe dichloromethane was removed under reduced pressure until a precipitate
  7. customto form
  8. customthe precipitate was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-dd064fe13c304d048f8985c83af1053f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

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