Water → N-[2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide hydrobromide

HRID 1097556Notes

Reaction equation

HRID 1097556 reaction equation
[N:1]#[C:2][Br:3].[NH2:4][C:5]1[C:6]([Cl:25])=[N:7][C:8]2[C:13]([C:14]=1[NH:15][CH2:16][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])([CH3:19])[CH3:18])=[CH:12][CH:11]=[CH:10][CH:9]=2.O>C(O)C>[BrH:3].[NH2:1][C:2]1[N:15]([CH2:16][C:17]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])([CH3:19])[CH3:18])[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([Cl:25])[C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 86626279HCID 86626279, compound

Product 1

HCID 86626280N-[2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide hydrobromideYield 15.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyanogen bromide (0.945 g, 8.93 mmol) was added to a solution of N-{2-[(3-amino-2-chloroquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide (2.55 g, 7.44 mmol) in ethanol (25 mL), and the solution was stirred at ambient temperature for two hours. An analysis by HPLC indicated that no reaction had taken place, and the reaction was then heated overnight at 90° C. and allowed to cool to ambient temperature. Water was added; a precipitate was present and was isolated by filtration and washed with diethyl ether to provide 510 mg of N-[2-(2-amino-4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide hydrobromide as a brown solid. The filtrate was concentrated under reduced pressure, and the residue was dissolved in methanol. Diethyl ether was added, and a gummy precipitate formed, which was dissolved again in methanol and concentrated under reduced pressure to provide an additional 1.1 g of the product as a dark brown solid.

Workup

  1. temperaturethe reaction was then heated overnight at 90° C.
  2. temperatureto cool to ambient temperature
  3. customwas isolated by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-d7f8ac93c90d40b2b089f86cff394aa0
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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