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

HRID 2383192Notes

Reaction equation

HRID 2383192 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]([CH3:33])([CH3:32])[CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:29]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pt].C(#N)C>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]([CH3:33])([CH3:32])[CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[NH2:29])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86626171Tert-butyl [2-(7-benzyloxy-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 95.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

tert-Butyl[2-(7-benzyloxy-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-78a7d95de4674599af06e5edd1cb4de1
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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