N,N'-Dimethylethylenediamine → 1-Acetyl-3-{5-chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}imidazolidin-2-one

HRID 2411361Notes

Reaction equation

HRID 2411361 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[O:10].[C:25]([N:28]1[CH2:32][CH2:31][NH:30][C:29]1=[O:33])(=[O:27])[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O.O1CCOCC1>[C:25]([N:28]1[CH2:32][CH2:31][N:30]([C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=2[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:29]1=[O:33])(=[O:27])[CH3:26]

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 79350N-AcetylimidazolidinoneHCID 58484730(2-Bromo-4-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

Product 1

HCID 584846831-Acetyl-3-{5-chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}imidazolidin-2-oneYield 70.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of (2-bromo-4-chlorophenyl) [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (817 mg) described in Preparation Example 167, 1-acetylimidazolidin-2-one (384 mg), tripotassium phosphate (849 mg) and copper(I) iodide (191 mg) were added dioxane (4 mL) and N,N′-dimethylethylenediamine (215 μL), and the mixture was stirred at 8 hr under refluxing. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The solvent was evaporated, and the residue was purified by column chromatography (ethyl acetate:methanol) to give the title compound (639 mg).

Workup

  1. temperatureunder refluxing
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography (ethyl acetate:methanol)

Sources & evidence

ORD record
ord-cab6f0f78c6847d6820a4fa96b0d2f98
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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