Valeryl chloride → N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:9][CH:8]=[C:7]([Br:20])[CH:6]=2.[C:21](Cl)(=O)[CH2:22][CH2:23][CH2:24][CH3:25]>N1C=CC=CC=1>[Br:20][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH2:14][NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[C:21]([CH2:22][CH2:23][CH2:24][CH3:25])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1Participants
Procedure
To a stirred solution of N-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]methanesulfonamide (46.4 g, 0.129 mol) in 1000 mL pyridine was slowly added valeryl chloride (1.1 equivalents). After 1.5 hours the mixture was yellow and turbid. The reaction mixture was then heated at reflux for 12 hours, allowed to cool to ambient temperature and concentrated under reduced pressure. The residue was mostly dissolved in 10% HCl to adjust to pH 1. The resulting suspension was adjusted to pH 12 with the addtion of 50% aqueous sodium hydroxide and stirred overnight. A precipitate formed and was isolated by filtration and air-dried to provide 45 g of N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide as a pale gray/green solid.
Workup
- temperatureThe reaction mixture was then heated
- temperatureat reflux for 12 hours
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was mostly dissolved in 10% HCl
- customA precipitate formed
- customwas isolated by filtration
- customair-dried
Sources & evidence
- ORD record
- ord-1e67f52d99c24395b2c4f5639b48571d
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598382B2
Reaction notes
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