m-Chloroperbenzoic acid → 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-5-oxido-1H-imidazo[4,5-c]quinoline
Reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([C:14]1[N:15]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:16]2[C:25]3[CH:24]=[CH:23][C:22]([O:26][CH2:27][C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[O:29])=[CH:21][C:20]=3[N:19]=[CH:18][C:17]=2[N:36]=1)[CH3:13]>C(Cl)(Cl)Cl>[CH2:12]([C:14]1[N:15]([CH2:37][CH:38]([CH3:39])[CH3:40])[C:16]2[C:25]3[CH:24]=[CH:23][C:22]([O:26][CH2:27][C:28]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)=[O:29])=[CH:21][C:20]=3[N+:19]([O-:9])=[CH:18][C:17]=2[N:36]=1)[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Over a period of 30 minutes, mCPBA (1.85 g, 5.47 mmol, 50% pure) was added in four portions to a solution of 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-1H-imidazo[4,5-c]quinoline (2.13 g, 5.47 mmol) in chloroform (200 mL). The reaction was stirred overnight at ambient temperature, washed twice with 1% aqueous sodium carbonate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol) to provide 0.53 g of 2-ethyl-1-(2-methylpropyl)-7-(2-morpholin-4-yl-2-oxoethoxy)-5-oxido-1H-imidazo[4,5-c]quinoline.
Workup
- washwashed twice with 1% aqueous sodium carbonate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)
Sources & evidence
- ORD record
- ord-e77b858a1d59443a84227d6006a15f46
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871782B2
Reaction notes
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