1-(2-Chloro-5-fluorophenyl)-5,5-dimethylpiperazin-2-one → N-{(S)-2-[4-(2-Chloro-5-fluorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1694933Notes

Reaction equation

HRID 1694933 reaction equation
[CH:1]([C@@H:4]1[CH2:8][C@@H:7]([CH:9]2[CH2:11][N@@:10]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[O:6][C:5]1=[O:24])([CH3:3])[CH3:2].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[N:33]1[CH2:38][C:37]([CH3:40])([CH3:39])[NH:36][CH2:35][C:34]1=[O:41]>C1(C)C=CC=CC=1>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[N:33]1[C:34](=[O:41])[CH2:35][N:36]([CH2:11][C@H:9]([NH:10][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[C@@H:7]2[CH2:8][C@@H:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:24])[O:6]2)[C:37]([CH3:40])([CH3:39])[CH2:38]1

Participants

4

Reactant 2

HCID 666453991-(2-Chloro-5-fluorophenyl)-5,5-dimethylpiperazin-2-oneHCID 178448140HCID 178448140, compound

Product 1

HCID 66645783N-{(S)-2-[4-(2-Chloro-5-fluorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.15 g of (3S,5S)-3-isopropyl-5-[(S)-1-(2-nitrobenzenesulfonyl)aziridin-2-yl]dihydrofuran-2-one obtained in Example (1g) (3.25 mmol) and 889 mg of 1-(2-chloro-5-fluorophenyl)-5,5-dimethylpiperazin-2-one obtained in Example (62d) (3.9 mmol) in toluene (32 ml) was stirred at 110° C. for one hour. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=10/1) to obtain 1.77 g of the title compound (yield: 91%).

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=10/1)

Sources & evidence

ORD record
ord-e8e6c654c3234a268590099a9d9cd35d
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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