Ethanol → 1-(6-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

HRID 9482

Reaction equation

[NH2:1][C:2]1[C:3](Cl)=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[CH:7][C:6]=2[Br:18].[CH2:20]([O:22][CH2:23][C:24](Cl)=O)[CH3:21].C(O)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[Br:18][C:6]1[C:5]2[N:4]=[CH:3][C:2]3[N:1]=[C:21]([CH2:20][O:22][CH2:23][CH3:24])[N:12]([CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[C:11]=3[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 1-(3-amino-8-bromo-2-chloroquinolin-4-ylamino)-2-methylpropan-2-ol (4.65 g, 14.4 mmol) and ethoxyacetyl chloride (1.9 mL, 15.8 mmol) in dichloromethane (72 mL) was stirred for one hour at ambient temperature. The solvent was removed under reduced pressure, and ethanol (43 mL), water (29 mL), and potassium carbonate (3.98 g, 28.8 mmol) were added. The reaction was stirred at 40° C. for 36 hours. The solvent was removed under reduce pressure, and the residue was diluted with water. The aqueous solution was extracted with chloroform, and the combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 4.4 g of 1-(6-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol as an orange solid.

Workup

additionwere added
customThe solvent was removed
additionthe residue was diluted with water
extractionThe aqueous solution was extracted with chloroform
dry with materialthe combined extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e4bc21a062524818a009f89c7b32cc59
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091214B2

Linked notes

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