Ethyl Acetate → HCID 57890373, compound

HRID 1820012Notes

Reaction equation

HRID 1820012 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:28][CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:28][CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])=[CH:23][CH:24]=3)=[O:15])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 23090912HCID 23090912, compound

Product 1

HCID 57890373HCID 57890373, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-chloro-N-[2-(4-methoxyphenyl)ethyl][1,1′-biphenyl]-4-carboxamide (700 mg, 1.91 mmol) obtained in Reference Example 22 in dichloromethane (10 ml) was added dropwise 1.0 mol/l solution (4.21 ml, 4.21 mmol) of boron tribromide in dichloroethane at 0° C., and the mixture was stirred at room temperature for 15 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to give a demethylated compound (620 mg). A solution of 4′-chloro-N-[2-(4-hydroxyphenyl)ethyl][1,1′-biphenyl]-4-carboxamide (620 mg), N-(2-chloroethyl)-N,N-diethylamine hydrochloride (364 mg, 2.11 mmol) and potassium carbonate (876 mg, 6.34 mmol) in dimethylformamide (10 ml) was stirred at room temperature for 6 hrs and at 100° C. for 4 days. Ethyl acetate was added to the reaction mixture, and the mixture was washed with 1N aqueous sodium hydroxide solution and brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by NH-silica column chromatography (developing solvent; chloroform:ethyl acetate:hexane=1:1:2), and powderized with isopropyl ether to give the title compound (318 mg).

Workup

  1. washthe mixture was washed with 1N aqueous sodium hydroxide solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe obtained residue was purified by NH-silica column chromatography (developing solvent; chloroform:ethyl acetate:hexane=1:1:2)

Sources & evidence

ORD record
ord-9ecf4db7372346d39b4030767d961435
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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