Isopropanol → Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamate

HRID 598327Notes

Reaction equation

HRID 598327 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([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:14]([N+:19]([O-])=O)[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)C.[H][H]>C1(C)C=CC=CC=1.[Pt]>[NH2:19][C:14]1[CH:15]=[N:16][C:17]2[C:12]([C:13]=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:11][CH:10]=[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:18]=2

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 69027554HCID 69027554, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 68900070Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamateYield 108.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Procedure

tert-Butyl [4-(7-benzyloxy-3-nitroquinolin-4-ylamino)butyl]carbamate (20.36 g, 43.6 mmol) was slurried in toluene (450 mL) and added to a Parr vessel charged with 5% platinum on carbon (4.3 g) and a small amount of toluene. 2-Propanol (50 mL) was added, and the vessel was charged with hydrogen (30 psi, 2.1×105 Pa). The hydrogen was replaced three times. After 4 hours, the catalyst was removed by filtration through a layer of CELITE filter aid, and the filter cake was rinsed with toluene (0.5 L), 50% toluene/2-propanol (0.5 L), and 2-propanol (0.25 L). The filtrate was concentrated under reduced pressure, and the residue was mixed with toluene and concentrated under reduced pressure to provide 20.7 g of tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamate as a viscous, black oil.

Workup

  1. additionadded to a Parr vessel
  2. customthe catalyst was removed by filtration through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was rinsed with toluene (0.5 L), 50% toluene/2-propanol (0.5 L), and 2-propanol (0.25 L)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionthe residue was mixed with toluene
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c41f31d90d0946098d89f9f72369c4b1
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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