m-Chloroperbenzoic acid → N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N'-isopropylurea

HRID 2383197Notes

Reaction equation

HRID 2383197 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[N:32]([CH2:33][C:34]([NH:37][C:38]([NH:40][CH:41]([CH3:43])[CH3:42])=[O:39])([CH3:36])[CH3:35])[C:31]([CH2:44][O:45][CH2:46][CH3:47])=[N:30][C:25]=3[CH:26]=[N:27][C:28]=2[CH:29]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[N:32]([CH2:33][C:34]([NH:37][C:38]([NH:40][CH:41]([CH3:43])[CH3:42])=[O:39])([CH3:35])[CH3:36])[C:31]([CH2:44][O:45][CH2:46][CH3:47])=[N:30][C:25]=3[CH:26]=[N+:27]([O-:9])[C:28]=2[CH:29]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 67051122N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N'-isopropylurea

Product 1

HCID 67051105N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N'-isopropylureaYield 108.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (60% pure, 1.18 g) was added to a solution of N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N′-isopropylurea (1.96 g, 4.0 mmol) in chloroform (50 mL). The reaction was stirred for 3 hours and then an additional 0.53 g of mCPBA was added. The reaction was stirred for 2 more hours and then quenched with aqueous 1% sodium carbonate. The layers were separated and the aqueous fraction was extracted with dichloromethane. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 2.2 g of crude N-[2-(7-benzyloxy-2-ethoxymethyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]-N′-isopropylurea as an orange foam.

Workup

  1. stirringThe reaction was stirred for 2 more hours
  2. customquenched with aqueous 1% sodium carbonate
  3. customThe layers were separated
  4. extractionthe aqueous fraction was extracted with dichloromethane
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84d612adba7e48ab9e21a46044dcfee2
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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