1,1,1-Trimethoxybutane → HCID 57447006, compound

HRID 2366591Notes

Reaction equation

HRID 2366591 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][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:21](OC)(OC)(OC)[CH2:22][CH2:23][CH3:24]>C1(C)C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:22]([C:21]1[N:12]([CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[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)[CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 57447009HCID 57447009, compound

Product 1

HCID 57447006HCID 57447006, compoundYield 83.4%

Reagents, catalysts & solvents 2

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

Procedure

A solution of ethyl 4-[(3-aminoquinolin-4-yl)amino]butanoate (49.7 g, 182 mmol, prepared as described in Parts A and B of Example 3) in toluene (500 mL) was heated at reflux for 10 minutes and then cooled slightly. Trimethyl orthobutyrate (29.0 g, 197 mmol) and pyridinium p-toluenesulfonate (0.70 g, 2.8 mmol) were added, and the reaction was heated at reflux under a Dean-Stark trap for 1.5 hours while the distillate was periodically removed. The reaction was allowed to stand overnight at ambient temperature. The toluene was removed under reduced pressure; chloroform (500 mL) and charcoal (4 g) were sequentially added. The resulting mixture was heated at reflux for one hour and then filtered through a layer of CELITE filter agent. The filtrate was washed with saturated aqueous sodium bicarbonate (100 mL), dried over potassium sulfate, filtered, and concentrated under reduced pressure to provide 49.4 g of ethyl 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanoate as a dark oil.

Workup

  1. temperatureat reflux for 10 minutes
  2. temperaturecooled slightly
  3. temperaturethe reaction was heated
  4. temperatureat reflux under a Dean-Stark trap for 1.5 hours while the distillate
  5. customwas periodically removed
  6. customThe toluene was removed under reduced pressure
  7. additionchloroform (500 mL) and charcoal (4 g) were sequentially added
  8. temperatureThe resulting mixture was heated
  9. temperatureat reflux for one hour
  10. filtrationfiltered through a layer of CELITE filter agent
  11. washThe filtrate was washed with saturated aqueous sodium bicarbonate (100 mL)
  12. dry with materialdried over potassium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-844f539132aa4d4b936e1e1a870f1fad
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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