tert-Butyl [2-(7-benzoyloxy-3-nitroquinolin-4-ylamino)-1,1-dimethylethyl]carbamate → Tert-butyl [2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]carbamate

HRID 598362Notes

Reaction equation

HRID 598362 reaction equation
[C:1]([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:23][CH2:24][C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:27])[CH3:26])=[C:15]([N+:20]([O-])=O)[CH:16]=[N:17]2)=[CH:12][CH:11]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pt].C(#N)C>[NH2:20][C:15]1[CH:16]=[N:17][C:18]2[C:13]([C:14]=1[NH:23][CH2:24][C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:26])[CH3:27])=[CH:12][CH:11]=[C:10]([O:9][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:19]=2

Participants

5

Reactant 2

HCID 86626173tert-Butyl [2-(7-benzoyloxy-3-nitroquinolin-4-ylamino)-1,1-dimethylethyl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 86626172Tert-butyl [2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]carbamateYield 98.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

tert-Butyl [2-(7-benzoyloxy-3-nitroquinolin-4-ylamino)-1,1-dimethylethyl]carbamate (6.74 g), 5% platinum on carbon (1.02 g), and acetonitrile (125 mL) were combined. The mixture was shaken overnight under 50 psi (3.4×105 Pa) of hydrogen. The reaction was filtered through CELITE filter agent and the filtrate was concentrated under reduced pressure to give 6.04 g of tert-butyl [2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]carbamate as an orange foam.

Workup

  1. filtrationThe reaction was filtered through CELITE
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f627269f7d5b4e43a37191a72cf4ebd4
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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