Ethoxyacetyl chloride → 1-[2-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-3-(2-methylethyl)urea

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Reaktionsgleichung

[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][NH:15][C:16]([NH:18][CH2:19][CH2:20][CH3:21])=[O:17])=[CH:9][CH:8]=[C:7]([Br:22])[CH:6]=2.[CH2:23]([O:25][CH2:26][C:27](Cl)=O)[CH3:24]>N1C=CC=CC=1>[Br:22][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH2:14][NH:15][C:16]([NH:18][CH2:19][CH2:20][CH3:21])=[O:17])[C:24]([CH2:23][O:25][CH2:26][CH3:27])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a stirred solution of 1-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]-3-(2-methylethyl)urea (27.2 g, 0.0743 mol) in 600 mL pyridine was slowly added ethoxyacetyl chloride (1.1 equivalents). After 1.5 hours the mixture was yellow and turbid. The reaction mixture was then heated at 80° C. for 12 hours and then concentrated under reduced pressure. The residue was dissolved in water and saturated aqueous potassium carbonate and stirred vigorously for three hours. A precipitate was present, was isolated by filtration, and air-dried for 48 hours to provide 32 g of 1-[2-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-3-(2-methylethyl)urea.

Aufarbeitung

concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in water
customwas isolated by filtration
customair-dried for 48 hours

Quellen und Nachweise

ORD-Eintrag: ord-223e941c0b2045cbafa9d0ab3301752e
Quelldatensatz: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07598382B2

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