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

HRID 9502

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-9312b9100a3448fd880c4a1e4f95c690
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091214B2

Linked notes

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