Pyridinium chloride → 2-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline
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
Procedure
A round bottom flask was charged with a magnetic stir bar, N-(4-{[-(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
- additionA round bottom flask was charged with a magnetic stir bar
- temperatureat reflux for 1.5 hours
- temperatureThe solution was cooled
- custompartitioned between ethyl acetate and water
- customThe layers were separated
- washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4db48f60f54e477a9ce26693f75cff51
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06664264B2
Reaction notes
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