HCID 86626162, compound → HCID 86626163, compound

HRID 598319Notes

Reaction equation

HRID 598319 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13]([N+:19]([O-])=O)=[C:12]2[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[Pt]>[NH2:19][C:13]1[CH:14]=[N:15][C:16]2[C:11]([C:12]=1[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH:18][CH:17]=2

Participants

4

Reactant 1

HCID 86626162HCID 86626162, compound

Product 1

HCID 86626163HCID 86626163, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

tert-Butyl [4-(6-benzyloxy-3-nitroquinolin-4-ylamino)butyl]carbamate (17.62 g, 37.77 mmol) was dissolved in toluene (600 mL) with heating and added to a Parr vessel charged with 5% platinum on carbon (2.20 g). The vessel was placed under hydrogen pressure (30 psi, 2.1×105 Pa) for three hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure to provide 15.5 g of tert-butyl {4-[3-amino-6-(benzyloxy)quinolin-4-ylamino]butyl}carbamate as a brown solid.

Workup

  1. temperaturewith heating
  2. additionadded to a Parr vessel
  3. customfor three hours
  4. filtrationThe reaction mixture was filtered through a layer of CELITE
  5. filtrationfilter aid
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8db2cde397154a21be72ac1583536afa
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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