Diethyl Oxalate → 5-(4-Methoxyphenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid ethyl ester

HRID 1437211노트

반응식

HRID 1437211 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=O.[H-].[Na+].[C:14]([O:21][CH2:22][CH3:23])(=[O:20])[C:15](OCC)=O.Cl.[NH:25]([C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[N:31][CH:32]=1)[NH2:26]>CN(C)C=O>[CH2:22]([O:21][C:14]([C:15]1[CH:1]=[C:2]([C:4]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=2)[N:25]([C:27]2[CH:32]=[N:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[N:26]=1)=[O:20])[CH3:23]

참가 물질

6

반응물 4

HCID 7268Diethyl OxalateHCID 74764'-MethoxyacetophenoneHCID 24758Sodium hydrideHCID 230902035-Hydrazinyl-2-methoxypyridine hydrochloride

생성물 1

HCID 579406405-(4-Methoxyphenyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Methoxyacetophenone (300 mg) was dissolved in N,N-dimethylformamide (4 mL). 60% Sodium hydride (160 mg) was added to the resultant mixture at 0° C., followed by stirring at room temperature for 0.5 hours. Under cooling with ice, diethyl oxalate (542 μL) was added to the reaction mixture, followed by stirring at room temperature for 14 hours. 5-Hydrazino-2-methoxypyridine hydrochloride (406 mg) obtained from Referential Example 1 was added to the reaction mixture, followed by stirring at 80° C. for 3 hours. The mixture was cooled in air. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was sequentially washed with water and saturated brine. Subsequently, the organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate), to thereby give the title compound as an oily substance (517 mg, 73%).

후처리

  1. additionwas added to the reaction mixture
  2. stirringby stirring at room temperature for 14 hours
  3. additionwas added to the reaction mixture
  4. stirringby stirring at 80° C. for 3 hours
  5. temperatureThe mixture was cooled in air
  6. customThe reaction mixture was partitioned between water and ethyl acetate
  7. washThe organic layer was sequentially washed with water and saturated brine
  8. dry with materialSubsequently, the organic layer was dried over sodium sulfate anhydrate
  9. filtrationfollowed by filtration
  10. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-246d1032772f40c4ae48fce2b31b8e30
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622471B2

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