Triethylamine → 8-benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinoline

HRID 2203488Notes

Reaction equation

HRID 2203488 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[CH:22][C:21]([NH:27][C:28](=O)[CH2:29][O:30][CH2:31][CH3:32])=[C:20]2[NH:34][CH2:35][CH2:36][CH3:37])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][C:24]2[N:23]=[CH:22][C:21]3[N:27]=[C:28]([CH2:29][O:30][CH2:31][CH3:32])[N:34]([CH2:35][CH2:36][CH3:37])[C:20]=3[C:19]=2[CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 67051145N-(6-benzyloxy-4-propylaminoquinolin-3-yl)-2-ethoxyacetamide hydrochloride

Product 1

HCID 670511278-benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolineYield 101.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (22.16 mL, 159.0 mmol) was added to a solution of N-(6-benzyloxy-4-propylaminoquinolin-3-yl)-2-ethoxyacetamide hydrochloride (16.1 g) in ethanol (265 mL), and the reaction mixture was heated at reflux and stirred for 3 hours. The reaction mixture was allowed to cool to ambient temperature. The ethanol was removed under reduced pressure and the residue dissolved in chloroform. The resulting solution was washed sequentially with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting oil was dissolved in acetonitrile and concentrated under reduced pressure to yield 14.32 g of 8-benzyloxy-2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinoline as a brown, crystalline solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux
  3. customThe ethanol was removed under reduced pressure
  4. dissolutionthe residue dissolved in chloroform
  5. washThe resulting solution was washed sequentially with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe resulting oil was dissolved in acetonitrile
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0abb015f48b241aead03b29cb755c79c
Source dataset
uspto-grants-2016_06
Patent number
US09365567B2

Reaction notes

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