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Phosphorus trichloride → 7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride

HRID 9445
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 9445
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:31][O:32][CH2:33][CH3:34])[N:14]([CH2:15][CH2:16][N+:17]3([O-])[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([Br:35])=[CH:5][C:4]=2[N:3]=1.P(Cl)(Cl)[Cl:37]>C(Cl)(Cl)Cl.O>[ClH:37].[ClH:37].[Br:35][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:14]([CH2:15][CH2:16][N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:13]([CH2:31][O:32][CH2:33][CH3:34])=[N:12][C:11]=3[C:2]([NH2:1])=[N:3][C:4]=2[CH:5]=1
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Komponenten

5

Edukt 2

HCID 24387Phosphorus trichlorideHCID 21984440tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate

Produkt 1

HCID 219841297-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochlorideAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterKatalysator
HCID 6212
Chloroform
Lösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

A solution of tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate (8.84 g, 16.1 mmol) in chloroform (400 mL) was cooled to 4° C. Phosphorous trichloride (9.82 mL, 113 mmol) was added dropwise, and the reaction was stirred for 45 minutes at 4° C. Water (one drop) was added to the reaction, which was allowed to warm to ambient temperature. The chloroform was removed under reduced pressure, and the residue was dissolved in ethanol (150 mL). Hydrogen chloride (21.5 mL of a 3 M solution in ethanol) was added, and the reaction was heated at reflux for 25 minutes. The reaction was allowed to cool to room temperature; a precipitate formed and was isolated by filtration to provide 6.86 g of 7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride as a light yellow solid.

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. customThe chloroform was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethanol (150 mL)
  4. additionHydrogen chloride (21.5 mL of a 3 M solution in ethanol) was added
  5. temperaturethe reaction was heated
  6. temperatureat reflux for 25 minutes
  7. temperatureto cool to room temperature
  8. customa precipitate formed
  9. customwas isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-fde1062fb7e5468ca3c9b1d8f714ccd0
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07091214B2

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