Acetonitrile → HCID 57515382, compound

HRID 547308Notes

Reaction equation

HRID 547308 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]1([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15]1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)CC)C.[CH2:27]([O:29][CH2:30][C:31](Cl)=O)[CH3:28].C(#N)C>ClCCl>[CH2:27]([O:29][CH2:30][C:31]1[N:12]([CH2:13][C:14]2([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15]2)[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)[CH3:28]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 574578101-{[(3-Aminoquinolin-4-yl)amino]methyl}cyclopentanol

Product 1

HCID 57515382HCID 57515382, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclopentanol (approximately 28.8 mmol) in dichloromethane (200 mL) at 0° C. was added triethylamine (4.41 mL, 31.6 mmol) and ethoxyacetyl chloride (88% purity, 3.96 g, 30.2 mmol). After 3 hours at room temperature, the solution was concentrated and ethanol (260 mL) and triethylamine (14 mL) were added. The resulting solution was heated at reflux for 18 hours and then concentrated under reduced pressure. The residue was partitioned between dichloromethane and water. The organic layer was washed with brine twice, dried over MgSO4, filtered, and concentrated to yield an oil that formed a white solid when acetonitrile was added. The mixture was sonicated briefly and filtered. The white powder was dried under vacuum to provide 4.55 g of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopentanol.

Workup

  1. concentrationthe solution was concentrated
  2. additionethanol (260 mL) and triethylamine (14 mL) were added
  3. temperatureThe resulting solution was heated
  4. temperatureat reflux for 18 hours
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was partitioned between dichloromethane and water
  7. washThe organic layer was washed with brine twice
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto yield an oil that
  12. additionwas added
  13. customThe mixture was sonicated briefly
  14. filtrationfiltered
  15. customThe white powder was dried under vacuum

Sources & evidence

ORD record
ord-2f9a39b671c74952a9bdb5f51686041a
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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