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4-Toluenesulfonyl chloride → tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

HRID 540815
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 540815
[OH-].[NH4+:2].[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:32][CH2:33][CH3:34])[C:9]2[C:18]3[CH:17]=[C:16]([O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:15]=[CH:14][C:13]=3[N+:12]([O-])=[CH:11][C:10]=2[N:31]=1)[CH3:4].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[C:25]([O:24][C:23](=[O:29])[NH:22][CH2:21][CH2:20][O:19][C:16]1[CH:15]=[CH:14][C:13]2[N:12]=[C:11]([NH2:2])[C:10]3[N:31]=[C:7]([CH2:6][O:5][CH2:3][CH3:4])[N:8]([CH2:32][CH2:33][CH3:34])[C:9]=3[C:18]=2[CH:17]=1)([CH3:28])([CH3:27])[CH3:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 68973926tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

Produkt 1

HCID 68974513tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

Ammonium hydroxide (50 mL) was added to a solution of tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate (9.7 g, 22 mmol) in dichloromethane (120 mL), and the mixture was cooled to 10° C. p-Toluenesulfonyl chloride (4.16 g, 21.8 mmol) was added in small portions, while maintaining the reaction temperature below 15° C. The reaction was stirred for 16 hours; a tan precipitate formed. Dichloromethane (500 mL) was added, and the precipitate was isolated by filtration and washed with diethyl ether to provide 3.98 g of tert-butyl[2-(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yloxy)ethyl]carbamate as a fine powder. The organic layer was washed sequentially with ammonium hydroxide, water, and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was recrystallized from acetonitrile to provide 4.4 g of tert-butyl 2-[(4-amino-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate as a peach-colored powder.

Aufarbeitung

  1. additionwas added in small portions
  2. temperaturewhile maintaining the reaction temperature below 15° C
  3. customa tan precipitate formed
  4. customthe precipitate was isolated by filtration
  5. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-18fae1a8b3644730a9dc8ce6c2da09b1
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871782B2

Notizen zur Reaktion

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