HCID 66958142, compound → Tert-butyl 3-[(3-amino-7-benzyloxy-quinolin-4-yl)amino]propylcarbamate

HRID 1364066Notes

Reaction equation

HRID 1364066 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][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[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>C(OCC)(=O)C.[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][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[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

4

Reactant 1

HCID 66958142HCID 66958142, compound

Product 1

HCID 66958474Tert-butyl 3-[(3-amino-7-benzyloxy-quinolin-4-yl)amino]propylcarbamateYield 93.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-[(7-benzyloxy-3-nitroquinolin-4-yl)amino]propylcarbamate (60.0 g, 132.6 mmol) was dissolved in ethyl acetate (400 mL) and transferred to a Parr hydrogenation vessel charged with 5% platinum on carbon (15.6 g, 80 mmol, 0.03 eq). The vessel was purged with nitrogen gas and placed under hydrogen pressure (50 psi, 3.45×105 Pa) overnight. The catalyst was removed by filtration through a layer of CELITE filter aid, and the filter cake was rinsed with methanol and dichloromethane. The filtrate was concentrated under reduced pressure to provide 52.4 g of tert-butyl 3-[(3-amino-7-benzyloxy-quinolin-4-yl)amino]propylcarbamate.

Workup

  1. customThe vessel was purged with nitrogen gas
  2. custompressure (50 psi, 3.45×105 Pa) overnight
  3. customThe catalyst was removed by filtration through a layer of CELITE
  4. filtrationfilter aid
  5. washthe filter cake was rinsed with methanol and dichloromethane
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d70bb33c4fd54a84a69ae3c93b06bcc6
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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