Trimethyl orthovalerate → 7-benzyloxy-2-butyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline

HRID 2383104Notes

Reaction equation

HRID 2383104 reaction equation
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]([NH:31][CH2:32][CH2:33][O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:25]([NH2:30])[CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][C:23]2[C:24]3[N:31]([CH2:32][CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:1]([CH2:2][CH2:3][CH2:4][CH3:5])=[N:30][C:25]=3[CH:26]=[N:27][C:28]=2[CH:29]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 83755Trimethyl orthovalerateHCID 670509287-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine

Product 1

HCID 670509737-benzyloxy-2-butyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolineYield 84%

Procedure

Under a nitrogen atmosphere, trimethyl orthovalerate (2.7 mL, 16 mmol) was added dropwise to a solution of 7-benzyloxy-N4-(2-phenoxyethyl)quinoline-3,4-diamine (3.0 g, 7.8 mmol), prepared as described in Parts A and B of Example 46, in xylenes (30 mL), and the reaction was heated at reflux for 24 hours. The reaction mixture was allowed to cool to ambient temperature; a precipitate formed, which was isolated by filtration, washed with hexanes, and dried for two hours in a vacuum oven to provide 2.96 g of 7-benzyloxy-2-butyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline.

Workup

  1. customprepared
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 24 hours
  4. customa precipitate formed
  5. customwhich was isolated by filtration
  6. washwashed with hexanes
  7. customdried for two hours in a vacuum oven

Sources & evidence

ORD record
ord-4286c457b9364ab5aa216a2c58984b13
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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