Ethanol → HCID 69506752, compound

HRID 2366615Notes

Reaction equation

HRID 2366615 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5](Cl)=O.[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:16][CH:15]=[CH:14][CH:13]=2.C(N(CC)CC)C.C(O)C>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 27597283-Methoxypropanoyl chlorideHCID 57447017HCID 57447017, compound

Product 1

HCID 69506752HCID 69506752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methoxypropionyl chloride (4.85 g, 39.8 mmol) was added dropwise over a period of ten minutes to a solution of ethyl 6-(3-aminoquinolin-4-ylamino)hexanoate (10.0 g, 33.2 mmol, prepared as described in Part A of Example 8) in dichloromethane (200 mL). The reaction was stirred for one hour at ambient temperature and then concentrated under reduced pressure. Triethylamine (18.49 g, 132.7 mmol) and ethanol (200 mL) were added, and the resulting solution was heated at reflux for three hours. The solvent was removed under reduced pressure. Dichloromethane (75 mL) was added, and the resulting solution was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 12.05 g of ethyl 6-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]hexanoate as a dark oil.

Workup

  1. customprepared
  2. concentrationconcentrated under reduced pressure
  3. temperaturethe resulting solution was heated
  4. temperatureat reflux for three hours
  5. customThe solvent was removed under reduced pressure
  6. additionDichloromethane (75 mL) was added
  7. washthe resulting solution was washed with saturated aqueous sodium bicarbonate
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4dcfe2ee90c04996af38033d2cbac759
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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