Valeryl chloride → N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide

HRID 9499

Reaction equation

HRID 9499 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]=1

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 21984309N-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]methanesulfonamide

Product 1

HCID 21984119N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 addition 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

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 12 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was mostly dissolved in 10% HCl
  5. additionThe resulting suspension was adjusted to pH 12 with the addition of 50% aqueous sodium hydroxide
  6. customA precipitate formed
  7. customwas isolated by filtration
  8. customair-dried

Sources & evidence

ORD record
ord-ab7b1d1d5bf34e299a5c6ee23d6d3cfb
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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