HCID 86626175, compound → HCID 86626176, compound

HRID 2383199Notes

Reaction equation

HRID 2383199 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]([CH3:33])([CH3:32])[CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:29]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pt].C(#N)C>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]([CH3:33])([CH3:32])[CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:19]=2)[N:14]=[CH:13][C:12]=1[NH2:29])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86626175HCID 86626175, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86626176HCID 86626176, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

tert-Butyl[2-(6-benzyloxy-3-nitroquinolin-4-ylamino)-1,1-dimethylethyl]carbamate (13.75 g), 5% platinum on carbon (1.03 g), and acetonitrile (250 mL) were combined. The mixture was shaken overnight under 50 psi (3.4×105 Pa) of hydrogen. The reaction was filtered through CELITE filter agent, and the filter pad was rinsed with acetonitrile. The filtrate was concentrated under reduced pressure. Residual water was removed by an azeotrope with toluene. Removal of all volatiles under reduced pressure provided 13.34 g of crude tert-butyl[2-(3-amino-6-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]carbamate as a brown foam.

Workup

  1. filtrationThe reaction was filtered through CELITE
  2. filtrationfilter agent
  3. washthe filter pad was rinsed with acetonitrile
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customResidual water was removed by an azeotrope with toluene
  6. customRemoval of all volatiles under reduced pressure

Sources & evidence

ORD record
ord-877a950ba1c24cfaaa7b6b2d5cb508e0
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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