HCID 86626162, compound → HCID 86626163, compound

HRID 2383147Notes

Reaction equation

HRID 2383147 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=2)[N:16]=[CH:15][C:14]=1[N+:31]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[Pt]>[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:21]=2)[N:16]=[CH:15][C:14]=1[NH2:31])([CH3:4])([CH3:2])[CH3:3]

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-7f8a72c1475f4939a29a04bd2b3e7302
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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