m-Chloroperbenzoic acid → 1-(2-methylpropyl)-5-oxido-2-propyl-7-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline

HRID 2203544Notes

Reaction equation

HRID 2203544 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([O:17][CH:18]4[CH2:22][CH2:21][O:20][CH2:19]4)=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH2:23][CH2:24][CH3:25].C1C=C(Cl)C=C(C(OO)=[O:35])C=1>>[CH3:1][CH:2]([CH3:26])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([O:17][CH:18]4[CH2:22][CH2:21][O:20][CH2:19]4)=[CH:11][C:10]=3[N+:9]([O-:35])=[CH:8][C:7]=2[N:6]=[C:5]1[CH2:23][CH2:24][CH3:25]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 689700041-(2-methylpropyl)-2-propyl-7-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 690851661-(2-methylpropyl)-5-oxido-2-propyl-7-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinolineYield 51.3%

Procedure

The method described in Part M of Example 2 was used to treat 1-(2-methylpropyl)-2-propyl-7-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline (1.1 g, 3.1 mmol) with mCPBA (1.07 g, 3.72 mmol). The crude product was purified by column chromatography on silica gel to afford 0.588 g of 1-(2-methylpropyl)-5-oxido-2-propyl-7-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline as a yellow solid.

Workup

  1. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ca47b30f249446c0842ddc05664cb5c9
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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