N-{2-[(2-chloro-3-nitroquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide → HCID 86626279, compound

HRID 1097555Notes

Reaction equation

HRID 1097555 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][CH2:16][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])([CH3:19])[CH3:18])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>[Pt].C(#N)C>[NH2:12][C:11]1[C:2]([Cl:1])=[N:3][C:4]2[C:9]([C:10]=1[NH:15][CH2:16][C:17]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])([CH3:19])[CH3:18])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 86626278N-{2-[(2-chloro-3-nitroquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide

Product 1

HCID 86626279HCID 86626279, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

N-{2-[(2-Chloro-3-nitroquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide (3.1 g, 8.3 mmol), 5% platinum on carbon (310 mg), and acetonitrile (40 mL) were added to a Parr vessel and shaken under hydrogen pressure (50 psi, 3.4×105 Pa) for four hours. An analysis by HPLC indicated the presence of starting material, and additional platinum on carbon (310 mg) was added. The reaction was shaken under hydrogen pressure overnight and filtered through a layer of CELITE filter agent. The filter cake was washed with dichloromethane, and the filtrate was concentrated under reduced pressure to provide 2.55 g of N-{2-[(3-amino-2-chloroquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide as a dark oil, which was used without purification.

Workup

  1. additionwas added
  2. stirringThe reaction was shaken under hydrogen pressure overnight
  3. filtrationfiltered through a layer of CELITE filter agent
  4. washThe filter cake was washed with dichloromethane
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f7ae37502814d5eb832664334f23320
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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