1,1,1-Trimethoxybutane → HCID 57447053, compound

HRID 2366659Notes

Reaction equation

HRID 2366659 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][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:29](OC)(OC)(OC)[CH2:30][CH2:31][CH3:32]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[CH2:30]([C:29]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[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)[CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 57447052HCID 57447052, compound

Product 1

HCID 57447053HCID 57447053, compoundYield 98.4%

Reagents, catalysts & solvents 1

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

Procedure

Ethyl 12-(3-aminoquinolin-4-ylamino)dodecanoate (20.0 g, 51.8 mmol) was treated according to a modification of the method described in Part B of Example 8. Prior to the addition of trimethyl orthobutyrate (9.53 mL, 59.6 mmol) and pyridinium p-toluenesulfonate (0.500 g, 1.99 mmol), the reaction was heated at reflux for ten minutes. After the reaction was heated at reflux, it was allowed to cool to ambient temperature, washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated under reduced pressure to provide 22.3 g of ethyl 12-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)dodecanoate, which was used without purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for ten minutes
  3. temperatureAfter the reaction was heated
  4. temperatureat reflux
  5. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c0cbf32466a41f78bb67e1fca3dfc33
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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