1,1,1-Trimethoxybutane → HCID 57447018, compound

HRID 2366598Notes

Reaction equation

HRID 2366598 reaction equation
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH3:4].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>[CH2:2]([C:1]1[N:39]([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]=1)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1235121,1,1-TrimethoxybutaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57447017HCID 57447017, compound

Product 1

HCID 57447018HCID 57447018, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trimethyl orthobutyrate (15.0 g, 49.8 mmol) and pyridinium p-toluenesulfonate (0.20 g, 0.80 mmol) were added to a solution ethyl 6-[(3-aminoquinolin-4-yl)amino]hexanoate (15.0 g, 49.8 mmol) in toluene (400 mL), and the reaction was heated at reflux under a Dean-Stark trap for 4.5 hours while the distillate was periodically removed. The reaction was allowed to cool to ambient temperature, washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide ethyl 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate, which was used without purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under a Dean-Stark trap for 4.5 hours while the distillate
  3. customwas periodically removed
  4. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0aba61e32b5044b8a7ee29ba1489e9a7
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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