N,N'-Dimethylethylenediamine → 3-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-3,5-difluorophenyl}oxazolidin-2-one

HRID 1804223Notes

Reaction equation

HRID 1804223 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[O:10])=[C:4]([F:25])[CH:3]=1.[O:26]1[CH2:30][CH2:29][NH:28][C:27]1=[O:31].C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:23][C:22]1[C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:9]([C:5]3[C:6]([F:8])=[CH:7][C:2]([N:28]4[CH2:29][CH2:30][O:26][C:27]4=[O:31])=[CH:3][C:4]=3[F:25])=[O:10])[CH2:12][CH2:13]2)=[N:18][CH:19]=[C:20]([CH3:24])[CH:21]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 739492-OxazolidinoneHCID 58484761(4-Bromo-2,6-difluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 673808853-{4-[4-(3,5-Dimethylpyridin-2-yl)piperazine-1-carbonyl]-3,5-difluorophenyl}oxazolidin-2-oneYield 55.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of (4-bromo-2,6-difluorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (410 mg) described in Preparation Example 60, oxazolidin-2-one (87 mg), potassium carbonate (277 mg) and copper (I) iodide (95.8 mg) were added toluene (1 mL) and N,N′-dimethylethylenediamine (101 μL), and the mixture was refluxed for 8 hr. Water was added to the reaction mixture, the mixture was extracted with chloroform, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (229.3 mg).

Workup

  1. temperaturethe mixture was refluxed for 8 hr
  2. extractionthe mixture was extracted with chloroform
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-4c32dbeac0ff4fe1a2c363e6455070e1
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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