Triethylamine → HCID 57515382, compound

HRID 44694Notes

Reaction equation

HRID 44694 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]>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

5

Reactant 3

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

Product 1

HCID 57515382HCID 57515382, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclopentanol (approximately 28.8 mmol, prepared as described above) in dichloromethane (200 mL) at 0° C. was added triethylamine (4.41 mL, 31.6 mmol) and ethoxyacetyl chloride (88%, 3.96 g, 30.2 mmol). After 3 h at rt, the solution was concentrated and ethanol (260 mL) and triethylamine (14 mL) were added. The resulting solution was heated at reflux for 18 h and then concentrated in vacuo. The residue was partitioned between dichloromethane and water. The organic layer was washed with brine twice and dried over MgSO4, filtered, and concentrated to 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 pure 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopentanol (4.55 g, 49% for three steps).

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 h
  5. concentrationconcentrated in vacuo
  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 to an oil that
  11. customformed a white solid when acetonitrile
  12. additionwas added
  13. customThe mixture was sonicated briefly
  14. filtrationfiltered
  15. customThe white powder was dried under vacuum

Sources & evidence

ORD record
ord-6f4a4c8714c84ada86eca2a398b4e6d7
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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