HCID 66958189, compound → HCID 66958650, compound

HRID 1364023Notes

Reaction equation

HRID 1364023 reaction equation
[CH3:1][C:2]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O>C(#N)C.[Pt]>[NH2:15][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:5]=1[NH:4][CH2:3][C:2]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:1])[CH3:18])=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 1

HCID 66958189HCID 66958189, compound

Product 1

HCID 66958650HCID 66958650, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of N-{1,1-dimethyl-2-[(3-nitroquinolin-4-yl)amino]ethyl}methanesulfonamide (4.0 g, 12 mmol) in acetonitrile (200 mL) was added to a Parr vessel charged with 5% platinum on carbon (0.5 g) and purged with nitrogen. The vessel was placed under hydrogen pressure (50 psi, 3.4×105 Pa) and shaken overnight. The reaction was filtered through a layer of CELITE filter aid, and the filter cake was washed with acetonitrile and dichloromethane until the filtrate was colorless. The filtrate was concentrated under reduced pressure to provide 3.51 g of N-{2-[(3-aminoquinolin-4-yl)amino]-1,1-dimethylethyl}methanesulfonamide as a yellow powder.

Workup

  1. custompurged with nitrogen
  2. filtrationThe reaction was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with acetonitrile and dichloromethane until the filtrate
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a530fb530a6478c88d826c8e31aa857
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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