Ethanol → 1-(6-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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-838dd0230bc34eb1be08fb46734ef3ea
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598382B2
Reaction notes
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