Benzenemethanamine, 3,4-dichloro- → {2-[4-(3,4-Dichlorobenzylamino)-2-methylquinolin-8-yloxy]-ethyl}-carbamate tert-butyl ester

HRID 1966515Notes

Reaction equation

HRID 1966515 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[C:18]([CH3:21])[CH:17]=[C:16]2Cl)([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:28][NH2:29]>CS(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[C:18]([CH3:21])[CH:17]=[C:16]2[NH:29][CH2:28][C:27]1[CH:30]=[CH:31][C:32]([Cl:33])=[C:25]([Cl:24])[CH:26]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 59474799[2-(4-Chloro-2-methylquinolin-8-yloxy)-ethyl]-carbamate tert-butyl ester

Product 1

HCID 25217468{2-[4-(3,4-Dichlorobenzylamino)-2-methylquinolin-8-yloxy]-ethyl}-carbamate tert-butyl esterYield 13%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

[2-(4-Chloro-2-methylquinolin-8-yloxy)-ethyl]-carbamate tert-butyl ester (1.30 g, 3.86 mmole), 3,4-dichlorobenzylamine (1.36 g, 7.72 mmole) and a catalytic effective amount of copper(II)sulphate pentahydrate in dimethylsulfoxide (0.2 mL) were stirred at 155° C. for 30 min in a microwave oven. The organic phases were washed with water and saturated NaCl solution, dried and the solvent was removed. The residue thus obtained was purified using silica gel chromatography, eluting with dichloromethane:water 90:10. Precipitation in ethyl acetate gave a brownish solid (230 mg, 13%).

Workup

  1. washThe organic phases were washed with water and saturated NaCl solution
  2. customdried
  3. customthe solvent was removed
  4. customThe residue thus obtained
  5. customwas purified
  6. washeluting with dichloromethane:water 90:10
  7. customPrecipitation in ethyl acetate

Sources & evidence

ORD record
ord-db73224190db4ce3aa61e008ea4ef7df
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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