Pyridinium chloride → 2-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline

HRID 1178273Notes

Reaction equation

HRID 1178273 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl.N1C=CC=CC=1>N1C=CC=CC=1>[CH2:21]([C:20]1[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][S:2][CH3:1])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 22320422N-(4-[{5-(methylthio)pentyl]amino}quinolin-3-yl)heptanamide

Product 1

HCID 223205532-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinolineYield 94.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A round bottom flask was charged with a magnetic stir bar, N-(4-{[5-(methylthio)pentyl]amino}quinolin-3-yl)heptanamide (4.44 g, 11.46 mmol), pyridine hydrochloride (0.13 g, 1.15 mmol), and anhydrous pyridine (50 mL) under a nitrogen atmosphere. The reaction was judged to be complete after stirring at reflux for 1.5 hours. The solution was cooled and partitioned between ethyl acetate and water. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford 2-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline (4.0 g, 10.82 mmol) as a brown oil which was used without further purification.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe solution was cooled
  4. custompartitioned between ethyl acetate and water
  5. customThe layers were separated
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90b4c252c81e482d99c6f4ff4df84844
Source dataset
uspto-grants-2007_10
Patent number
US07276515B2

Reaction notes

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