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

HRID 540900Notes

Reaction equation

HRID 540900 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>[Pt].C1(C)C=CC=CC=1.CC(O)C>[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

5

Reactant 1

HCID 69027554HCID 69027554, compound

Product 1

HCID 68900070Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamateYield 99.8%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of tert-butyl 4-{[7-(benzyloxy)-3-nitroquinolin-4-yl]amino}butylcarbamate (30.0 g, 64.3 mmol) and 5% platinum on carbon (3.0 g) in toluene (675 mL) and 2-propanol (100 mL) was hydrogenated on a Parr apparatus for 12.5 hours at 24 psi (1.7×105 Pa). The mixture was filtered through CELFTE filter agent, which was rinsed afterwards with 1:1 toluene/2-propanol and 2-propanol. The combined filtrates were concentrated under reduced pressure to afford 28 g of tert-butyl 4-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}butylcarbamate as a viscous black oil that was used in the next step without purification.

Workup

  1. filtrationThe mixture was filtered through CELFTE
  2. filtrationfilter agent, which
  3. washwas rinsed afterwards with 1:1 toluene/2-propanol and 2-propanol
  4. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-f98b514f67e54c77920d994e108d33d1
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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