Tert-butyl[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]carbamate → HCID 66957881, compound

HRID 1818183Notes

Reaction equation

HRID 1818183 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:7]([N+:12]([O-])=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1>C(#N)C.C(O)(C)C.[Pt]>[NH2:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([C:6]=1[NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2

Participants

5

Reactant 1

HCID 21984156Tert-butyl[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]carbamate

Product 1

HCID 66957881HCID 66957881, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl [2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]carbamate (165.0 g, 401.2 mmol) in acetonitrile (3.3 L) and isopropanol (990 mL) and 5% platinum on carbon (13.2 g) were added to a Parr vessel, which was placed under hydrogen pressure (50 psi, 3.4×105 Pa) overnight. The mixture was filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure to provide 139.29 g of tert-butyl [2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]carbamate as a yellow solid. The product was suspended in a mixture of dichloromethane (4 mL/g) and chloroform (8 mL/g), and the suspension was divided into two equal portions.

Workup

  1. custompressure (50 psi, 3.4×105 Pa) overnight
  2. filtrationThe mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b4336f93ce8f46caa12f0234329e5c5c
Source dataset
uspto-grants-2009_10
Patent number
US07598382B2

Reaction notes

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