N-[1,1-Dimethyl-2-(3-nitro-7-benzyloxyquinolin-4-ylamino)ethyl]methanesulfonamide → N-[2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]methanesulfonamide

HRID 2383115Notes

Reaction equation

HRID 2383115 reaction equation
[CH3:1][C:2]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])([CH3:26])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[N+:23]([O-])=O>[Pt].C(#N)C>[NH2:23][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:5]=1[NH:4][CH2:3][C:2]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])([CH3:26])[CH3:1])=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH:10]=2

Participants

4

Reactant 1

HCID 67050936N-[1,1-Dimethyl-2-(3-nitro-7-benzyloxyquinolin-4-ylamino)ethyl]methanesulfonamide

Product 1

HCID 67050976N-[2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]methanesulfonamideYield 91.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

N-[1,1-Dimethyl-2-(3-nitro-7-benzyloxyquinolin-4-ylamino)ethyl]methanesulfonamide (14.8 g, 33.3 mmol) was mixed with acetonitrile (300 mL) and added to a Parr flask; 5% platinum on carbon (2 g) was added. The reaction was flushed with nitrogen and placed under hydrogen pressure (40 psi, 2.8×105 Pa) for 5.5 hours with the hydrogen replaced after two hours. An analysis by TLC indicated the presence of starting material. Additional acetonitrile (200 mL) and 5% platinum on carbon (2 g) were added, and the reaction was placed under hydrogen pressure overnight. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with acetonitrile. The filtrate was concentrated under reduced pressure. Toluene and dichloromethane were added and removed under reduced pressure twice to yield 12.6 g of N-[2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]methanesulfonamide as a foam.

Workup

  1. additionadded to a Parr flask
  2. customThe reaction was flushed with nitrogen
  3. customfor 5.5 hours
  4. additionAdditional acetonitrile (200 mL) and 5% platinum on carbon (2 g) were added
  5. custompressure overnight
  6. filtrationThe reaction mixture was filtered through a layer of CELITE
  7. filtrationfilter aid
  8. washthe filter cake was washed with acetonitrile
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. additionToluene and dichloromethane were added
  11. customremoved under reduced pressure twice

Sources & evidence

ORD record
ord-f42b84c6886746c1a6a22e7db18ea093
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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