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

HRID 2366603Notes

Reaction equation

HRID 2366603 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:23](OC)(OC)(OC)[CH2:24][CH2:25][CH3:26]>C1(C)C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:24]([C:23]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 57447017HCID 57447017, compound

Product 1

HCID 57447018HCID 57447018, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolvent

Procedure

A solution of ethyl 6-[(3-aminoquinolin-4-yl)amino]hexanoate (44.0 g, 146 mmol) in toluene (500 mL) was heated at reflux under a Dean-Stark trap for 1.5 hours and then allowed to cool to ambient temperature. Trimethyl orthobutyrate (29.2 mL, 182.5 mmol) and pyridinium p-toluenesulfonate (0.300 g, 1.20 mmol) were sequentially added, and the reaction was heated at reflux for three 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. The crude product was purified by column chromatography on silica gel (eluting with 97:3 dichloromethane:methanol) to provide 38 g of ethyl 6-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)hexanoate.

Workup

  1. temperatureat reflux under a Dean-Stark trap for 1.5 hours
  2. temperaturethe reaction was heated
  3. temperatureat reflux for three hours
  4. temperatureto cool to ambient temperature
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washthe resulting solution was washed sequentially with saturated aqueous sodium bicarbonate and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by column chromatography on silica gel (eluting with 97:3 dichloromethane:methanol)

Sources & evidence

ORD record
ord-69f618cabeac48e59f9075744f05d758
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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