4-Toluenesulfonyl chloride → N-[2-(4-amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-ethyl]methanesulfonamide

HRID 1818246

Reaktionsgleichung

Reaktionsgleichung von HRID 1818246
ClC1C=C(C=CC=1)C(OO)=O.[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[C:17]3[N:25]([CH2:26][CH2:27][NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[C:24]([CH2:33][CH2:34][CH2:35][CH3:36])=[N:23][C:18]=3[CH:19]=[N:20][C:21]=2[CH:22]=1.[OH-].[NH4+:38].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[NH2:38][C:19]1[C:18]2[N:23]=[C:24]([CH2:33][CH2:34][CH2:35][CH3:36])[N:25]([CH2:26][CH2:27][NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[C:17]=2[C:16]2[CH:15]=[CH:14][C:13]([Br:12])=[CH:22][C:21]=2[N:20]=1

Komponenten

8

Edukt 5

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 21984119N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide

Produkt 1

HCID 21984323N-[2-(4-amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-ethyl]methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Chloroperoxybenzoic acid (1.0 equivalent of 50% pure material) was added to a solution of N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide (44 g, 103.4 mmol) in 1000 mL dichloromethane. After 2 hours, concentrated ammonium hydroxide solution (600 mL) was added. The reaction was stirred for 15 minutes before p-toluenesulfonyl chloride (1.1 equivalents) was slowly added in small portions. The reaction was stirred overnight at room temperature and then water and potassium carbonate were added with vigorous stirring. A precipitate formed and was isolated by filtration to provide N-[2-(4-amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-ethyl]methanesulfonamide.

Aufarbeitung

  1. additionwas slowly added in small portions
  2. customA precipitate formed
  3. customwas isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-04150da487e749ff80b7de19a1018872
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598382B2

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