Sodium hydride → 2-(5-Chloro-3-Nitro-Pyridin-2-Yloxy)-1-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]Ethanone

HRID 11716노트

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HRID 11716 반응식
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C@@H:12]([CH3:13])[CH2:11][N:10]([C:14](=[O:17])[CH2:15][OH:16])[C@H:9]([CH3:18])[CH2:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:24]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][C:27]([Cl:33])=[CH:26][N:25]=1>C1(C)C=CC=CC=1>[Cl:33][C:27]1[CH:28]=[C:29]([N+:30]([O-:32])=[O:31])[C:24]([O:16][CH2:15][C:14]([N:10]2[CH2:11][C@H:12]([CH3:13])[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:20][CH:19]=3)[CH2:8][C@H:9]2[CH3:18])=[O:17])=[N:25][CH:26]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 80633312,5-Dichloro-3-nitropyridineHCID 234058381-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-hydroxy-ethanone

생성물 1

HCID 696556572-(5-Chloro-3-Nitro-Pyridin-2-Yloxy)-1-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]Ethanone수율 89.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of 1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-hydroxy-ethanone (0.90 g, 3.2 mmol) in toluene (20 mL) at 0° C. was added sodium hydride (0.18 g, 4.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 15 minutes, then 2,5-dichloro-3-nitro-pyridine (0.65 g, 3.38 mmol) was added and the solution was stirred at ambient temperature for 18 hours. The reaction was quenched by the slow addition of water (5 mL) then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel gave the title compound (1.25 g).

후처리

  1. stirringthe solution was stirred at ambient temperature for 18 hours
  2. customThe reaction was quenched by the slow addition of water (5 mL)
  3. extractionthen extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2a0344112e3c4eae845fa2698f0127bd
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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