Ethyl orthoformate → HCID 57447025, compound

HRID 2366609Notes

Reaction equation

HRID 2366609 reaction equation
[CH:1](OCC)(OCC)OCC.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[NH2:28][C:29]1[CH:30]=[N:31][C:32]2[C:37]([C:38]=1[NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:36][CH:35]=[CH:34][CH:33]=2>C1(C)C=CC=CC=1>[N:39]1([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:38]2[C:37]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[N:31]=[CH:30][C:29]=2[N:28]=[CH:1]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57447017HCID 57447017, compound

Product 1

HCID 57447025HCID 57447025, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethyl orthoformate (12.74 mL, 76.64 mmol) and pyridinium p-toluenesulfonate (0.200 g) were sequentially added to a solution of ethyl 6-[(3-aminoquinolin-4-yl)amino]hexanoate (16.5 g, 54.7 mmol, prepared as described in Part A of Example 8) in toluene (200 mL), and the reaction was heated at reflux under a Dean-Stark trap for four hours, allowed to cool to ambient temperature, and concentrated under reduced pressure. The residue was dissolved in dichloromethane, and the resulting solution was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 16.4 g of ethyl 6-(1H-imidazo[4,5-c]quinolin-1-yl)hexanoate.

Workup

  1. customprepared
  2. temperaturethe reaction was heated
  3. temperatureat reflux under a Dean-Stark trap for four hours
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washthe resulting solution was washed sequentially with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6d712a622ad45088b50b87fa89d3647
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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