N-(2-{[7-(benzyloxy)-3-nitroquinolin-4-yl]amino}-1,1-dimethylethyl)-N'-isopropylurea → N-(2-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}-1,1-dimethylethyl)-N'-isopropylurea

HRID 540874Notes

Reaction equation

HRID 540874 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:22][CH2:23][C:24]([NH:27][C:28]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:29])([CH3:26])[CH3:25])=[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].C(#N)C>[NH2:19][C:14]1[CH:15]=[N:16][C:17]2[C:12]([C:13]=1[NH:22][CH2:23][C:24]([NH:27][C:28]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:29])([CH3:26])[CH3:25])=[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 69507170N-(2-{[7-(benzyloxy)-3-nitroquinolin-4-yl]amino}-1,1-dimethylethyl)-N'-isopropylurea

Product 1

HCID 69507214N-(2-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}-1,1-dimethylethyl)-N'-isopropylureaYield 92.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(2-{[7-(benzyloxy)-3-nitroquinolin-4-yl]amino}-1,1-dimethylethyl)-N′-isopropylurea (4.24 g, 9.39 mmol) and 5% platinum on carbon (1.0 g) in acetonitrile (700 mL) was hydrogenated at 30 psi (2.1×105 Pa) overnight on a Parr apparatus. The mixture was filtered through CELITE filter agent, which was subsequently rinsed with acetonitrile and dichloromethane. The filtrate was concentrated under reduced pressure to yield 3.67 g of N-(2-{[3-amino-7-(benzyloxy)quinolin-4-yl]amino}-1,1-dimethylethyl)-N′-isopropylurea as a pale yellow foam that was used without purification.

Workup

  1. customwas hydrogenated at 30 psi (2.1×105 Pa) overnight on a Parr apparatus
  2. filtrationThe mixture was filtered through CELITE
  3. filtrationfilter agent, which
  4. washwas subsequently rinsed with acetonitrile and dichloromethane
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aae990822c3f4f6e8fed87d373e68c23
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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