Sodium hydride → 5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehyde

HRID 11681노트

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HRID 11681 반응식
[H-].[Na+].[F:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C@@H:14]([CH3:15])[CH2:13][N:12]([C:16](=[O:19])[CH2:17][OH:18])[C@H:11]([CH3:20])[CH2:10]2)=[CH:6][CH:5]=1.Cl[C:24]1[C:29]([CH:30]=[O:31])=[CH:28][C:27]([Cl:32])=[CH:26][N:25]=1>C1(C)C=CC=CC=1>[Cl:32][C:27]1[CH:28]=[C:29]([CH:30]=[O:31])[C:24]([O:18][CH2:17][C:16]([N:12]2[CH2:13][C@H:14]([CH3:15])[N:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:22][CH:21]=3)[CH2:10][C@H:11]2[CH3:20])=[O:19])=[N:25][CH:26]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 219732742,5-Dichloro-pyridine-3-carbaldehydeHCID 234058381-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-hydroxy-ethanone

생성물 1

HCID 865911655-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehyde수율 67.1%

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
0 °C

실험 절차

To a 0° C. suspension of sodium hydride (60% dispersion in mineral oil, 0.031 g, 0.78 mmol) in toluene (3 mL) was added 1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-hydroxy-ethanone (0.20 g, 0.71 mmol) in toluene (2 mL). The reaction mixture was stirred at 0° C. for 30 minutes, and then treated with 2,5-dichloro-pyridine-3-carbaldehyde (0.14 g, 0.78 mmol). The resulting mixture was refluxed for 4 hours, cooled to ambient temperature and washed with saturated aqueous sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography provided the title compound (0.20 g).

후처리

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. temperaturecooled to ambient temperature
  3. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8d2580975c9440d99c5df9cc611230c9
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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