N,N'-Dimethylethylenediamine → HCID 24906058, compound

HRID 1868096Notes

Reaction equation

HRID 1868096 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[C:20]1[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:20]3[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=3)[C:14](=[O:18])[CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 51938202-bromo-3-trifluoromethylpyridineHCID 30328636HCID 30328636, compound

Product 1

HCID 24906058HCID 24906058, compoundYield 10%

Reagents, catalysts & solvents 2

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

Procedure

Amidation of 4-(3,4-dichloro-benzenesulfonyl)-piperazin-2-one (150 mg, 0.49 mmol) with 2-bromo-3-trifluoromethyl pyridine (164.5 mg, 0.73 mmol) was carried out according to a similar procedure described for example 15A using powdered anhydrous potassium carbonate (134.1 mg, 0.97 mmol) as base, CuI (9.2 mg, 0.049 mmol) as catalyst, N,N′-dimethyl-1,2-ethylenediamine (5.2 μL, 0.049 mmol) as ligand, and anhydrous 1,4-dioxane (1.8 mL) as solvent. 4-(3,4-dichloro-benzenesulfonyl)-1-(3-trifluoromethyl-pyridin-2-yl)-piperazin-2-one was obtained in 10% yield (21 mg) as an off-white solid.

Sources & evidence

ORD record
ord-07033dd4b697408e8fc16e015be2c88b
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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