Water → 1-(cyclopropylmethyl)-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 333731노트

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HRID 333731 반응식
[I-].[Na+].Cl[Si](C)(C)C.[CH:8]1([CH2:11][N:12]2[CH:17]=[C:16]([O:18]C)[C:15](=[O:20])[C:14]([C:21]3[N:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:24]=[CH:23][CH:22]=3)=[N:13]2)[CH2:10][CH2:9]1.O>C(#N)C>[CH:8]1([CH2:11][N:12]2[CH:17]=[C:16]([OH:18])[C:15](=[O:20])[C:14]([C:21]3[N:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:24]=[CH:23][CH:22]=3)=[N:13]2)[CH2:9][CH2:10]1

참가 물질

6

반응물 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 680148501-(cyclopropylmethyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

생성물 1

HCID 895865391-(cyclopropylmethyl)-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one수율 79.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of sodium iodide (3.75 g) in acetonitrile (150 mL) was added chlorotrimethylsilane (3.17 mL) with stirring at room temperature for 30 min. Then, 1-(cyclopropylmethyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (1.613 g) was added, and the mixture was stirred for 30 min at the same temperature and further refluxed for 4 hr. The reaction mixture was allowed to cool to room temperature, poured into water and the mixture was stirred for 30 min. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was triturated with diisopropyl ether, collected by filtration, washed successively with ethyl acetate and diisopropyl ether, and dried to give the title compound (1.23 g) as a pale-brown solid.

후처리

  1. stirringthe mixture was stirred for 30 min at the same temperature
  2. temperaturefurther refluxed for 4 hr
  3. temperatureto cool to room temperature
  4. stirringthe mixture was stirred for 30 min
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was triturated with diisopropyl ether
  10. filtrationcollected by filtration
  11. washwashed successively with ethyl acetate and diisopropyl ether
  12. customdried

출처 및 근거

ORD 기록
ord-8282ed1d7daf40b9b21ba2dcba3dcbbb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883788B2

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