Ethyl 2,4-dioxo-4-(pyridin-2-yl)butanoate → 5-Hydroxy-1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)-4,5-dihydropyrazole-3-carboxylic acid ethyl ester

HRID 1437209

반응식

HRID 1437209 반응식
[CH2:1]([O:3][C:4](=[O:16])[C:5](=O)[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8])[CH3:2].[NH:17]([C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[N:23][CH:24]=1)[NH2:18]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH2:6][C:7]([OH:8])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:17]([C:19]2[CH:24]=[N:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:18]=1)=[O:16])[CH3:2]

참가 물질

4

반응물 2

HCID 12171345Ethyl 2,4-dioxo-4-(pyridin-2-yl)butanoateHCID 222178535-Hydrazinyl-2-methoxypyridine

생성물 1

HCID 231436765-Hydroxy-1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)-4,5-dihydropyrazole-3-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

4-(2-Pyridyl)-2,4-dioxobutanoic acid ethyl ester (1.10 g) obtained from Referential Example 31 and 5-hydrazino-2-methoxypyridine (0.692 g) obtained from Referential Example 2 were dissolved in ethanol (22 mL). The resultant mixture was refluxed under heat for 14 hours, followed by cooling in air. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), followed by purification through silica gel column chromatography (toluene-acetone), to thereby give 5-hydroxy-1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)-4,5-dihydropyrazole-3-carboxylic acid ethyl ester as a solid substance (0.575 g, 34%).

후처리

  1. temperatureunder heat for 14 hours
  2. temperatureby cooling in air
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  5. customfollowed by purification through silica gel column chromatography (toluene-acetone)

출처 및 근거

ORD 기록
ord-170b13e042244dee9a638a215342bbcf
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07622471B2

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