1-(2,6-Difluorophenyl)-5,5-dimethylpiperazin-2-one → HCID 66645601, compound

HRID 1694969Notes

Reaction equation

HRID 1694969 reaction equation
[CH3:1][C@@H:2]1[CH2:6][C@@H:5]([CH:7]2[CH2:9][N@@:8]2[S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[O:4][C:3]1=[O:22].[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=1[N:31]1[CH2:36][C:35]([CH3:38])([CH3:37])[NH:34][CH2:33][C:32]1=[O:39]>C1(C)C=CC=CC=1>[F:30][C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([F:23])[C:25]=1[N:31]1[C:32](=[O:39])[CH2:33][N:34]([CH2:9][C@H:7]([NH:8][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C@@H:5]2[CH2:6][C@@H:2]([CH3:1])[C:3](=[O:22])[O:4]2)[C:35]([CH3:38])([CH3:37])[CH2:36]1

Participants

4

Reactant 2

HCID 666456401-(2,6-Difluorophenyl)-5,5-dimethylpiperazin-2-oneHCID 178461437HCID 178461437, compound

Product 1

HCID 66645601HCID 66645601, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 600 mg of (3R,5S)-3-methyl-5-[(S)-1-(2-nitrobenzenesulfonyl)aziridin-2-yl]dihydrofuran-2-one obtained in Example (76g) (1.84 mmol) and 574 mg of 1-(2,6-difluorophenyl)-5,5-dimethylpiperazin-2-one obtained in Example (60d) (2.40 mmol) in toluene (18 ml) was stirred at 110° C. for two hours. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1) to obtain 1.03 g of the title compound (yield: 99%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1)

Sources & evidence

ORD record
ord-5781f877cd7641bf9f5ee320a469a574
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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