Hydrogen Peroxide → HCID 67382408, compound

HRID 909344Notes

Reaction equation

HRID 909344 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:24][CH2:25][CH2:26][O:27][CH:28]([CH3:30])[CH3:29])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:23]=1)[CH3:2].C(#N)C1C=CC=CC=1.C(=O)(O)[O-:40].[Na+].OO>CO>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:24][CH2:25][CH2:26][O:27][CH:28]([CH3:29])[CH3:30])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:12][C:11]=3[N+:10]([O-:40])=[CH:9][C:8]=2[N:23]=1)[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 7505BenzonitrileHCID 516892Sodium BicarbonateHCID 67382101HCID 67382101, compound

Product 1

HCID 67382408HCID 67382408, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Ethoxymethyl-1-(3-isopropoxypropyl)-7-(morpholin-4-yl)-1H-imidazo[4,5-c]quinoline (1.0 g), benzonitrile (0.44 mL) and sodium bicarbonate (0.15 g) were slurried in methanol. Hydrogen peroxide (55% by weight in water, 0.395 mL) was added dropwise over 1 hour. The reaction was stirred overnight. The methanol was removed under reduced pressure and the residue was purified by column chromatography on a Biotage Horizon™ High Performance Flash Chromatography instrument. The purification was carried out eluting with chloroform:CMA in a gradient from 98:2 to 75:25. 2-Ethoxymethyl-1-(3-isopropoxypropyl)-7-(morpholin-4-yl)-1H-imidazo[4,5-c]quinoline 5-oxide was isolated as a yellow oil (0.166 g).

Workup

  1. customThe methanol was removed under reduced pressure
  2. customthe residue was purified by column chromatography on a Biotage Horizon™ High Performance Flash Chromatography instrument
  3. customThe purification
  4. washwas carried out eluting with chloroform

Sources & evidence

ORD record
ord-89c50d75d6684f37981cf0b6672c0e0b
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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