HCID 69027554, compound → Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamate

HRID 2383111Notes

Reaction equation

HRID 2383111 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][C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[N+:31]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[H][H]>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][C:19]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[NH2:31])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 69027554HCID 69027554, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68900070Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamateYield 76.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Procedure

tert-Butyl[4-(7-benzyloxy-3-nitroquinolin-4-ylamino)butyl]carbamate (39.92 g, 85.57 mmol) was dissolved in toluene (1700 mL) and added to a Parr vessel charged with 5% platinum on carbon (3.9 g) and a small volume of toluene. The vessel was placed under hydrogen pressure (50 psi, 3.4×105 Pa). The hydrogen was replaced three times, and the reaction was shaken overnight. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with ethanol (700 mL). The filtrate was concentrated under reduced pressure to provide 28.62 g of tert-butyl{4-[3-amino-7-(benzyloxy)quinolin-4-ylamino]butyl}carbamate as a brown solid.

Workup

  1. additionadded to a Parr vessel
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with ethanol (700 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f989f1e55b474842ae04c8884a5f91fd
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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