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Tetrabutylammonium Fluoride → (S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {5-[1-(2-hydroxy-ethyl)-5-methyl-1H-pyrazol-3-yl]-2-methyl-phenyl}-amide

HRID 1697882
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HRID 1697882 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[O:24][CH2:25][CH2:26][N:27]1[C:31]([CH3:32])=[CH:30][C:29]([C:33]2[CH:34]=[CH:35][C:36]([CH3:56])=[C:37]([NH:39][C:40]([C:42]3[C@H:47]([C:48]4[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=4)[CH2:46][C:45](=[O:55])[NH:44][CH:43]=3)=[O:41])[CH:38]=2)=[N:28]1)(C)(C)C>C1COCC1>[OH:24][CH2:25][CH2:26][N:27]1[C:31]([CH3:32])=[CH:30][C:29]([C:33]2[CH:34]=[CH:35][C:36]([CH3:56])=[C:37]([NH:39][C:40]([C:42]3[C@H:47]([C:48]4[CH:49]=[CH:50][C:51]([F:54])=[CH:52][CH:53]=4)[CH2:46][C:45](=[O:55])[NH:44][CH:43]=3)=[O:41])[CH:38]=2)=[N:28]1
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참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 67277422(S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid (5-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-phenyl)-amide

생성물 1

HCID 53239311(S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {5-[1-(2-hydroxy-ethyl)-5-methyl-1H-pyrazol-3-yl]-2-methyl-phenyl}-amide수율 45.6%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

A solution tetrabutylammonium fluoride (1M in THF) was added drop wise to a 0° C. solution of (S)-4-(4-Fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid (5-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-pyrazol-3-yl}-2-methyl-phenyl)-amide (66 mg) in THF. The mixture was stirred at 0° C. for five minutes and then stirred at room temperature for 18 hours. The mixture was partitioned between water and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (0 to 8% CH3OH in CH2Cl2) gave 24 mg of (S)-4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid {5-[1-(2-hydroxy-ethyl)-5-methyl-1H-pyrazol-3-yl]-2-methyl-phenyl}-amide as a solid, MS (M+H)=419.

후처리

  1. stirringstirred at room temperature for 18 hours
  2. customThe mixture was partitioned between water and EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification of the crude product by flash chromatography (0 to 8% CH3OH in CH2Cl2)

출처 및 근거

ORD 기록
ord-149fde5200004f31b68db31919296133
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163929B2

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