Glyoxal → 8-(4-Fluorophenyl)-7-(pyridin-4-yl)pyrazolo[1,5-b][1,2,4]triazine

HRID 54943

반응식

HRID 54943 반응식
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:32])(=O)=O.[CH:34]([CH:36]=O)=O.C(=O)(O)[O-].[Na+]>C(O)C.O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:3]2[C:4]([C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)=[N:5][N:6]3[C:2]=2[N:1]=[CH:36][CH:34]=[N:32]3)=[CH:14][CH:15]=1

참가 물질

7

반응물 4

HCID 7860GlyoxalHCID 516892Sodium BicarbonateHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 178509114HCID 178509114, 화합물

생성물 1

HCID 199572708-(4-Fluorophenyl)-7-(pyridin-4-yl)pyrazolo[1,5-b][1,2,4]triazine

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of 5-amino-4-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazole (1.674 g) in ethanol (33 ml) was added O-mesitylsulfonylhydroxylamine (2.362 g). The mixture was stirred at ambient temperature for 30 minutes and to the mixture was added a solution of glyoxal in water (40%, 955 mg). The mixture was refluxed for 4 hours and cooled. The reaction mixture was poured into an aqueous saturated sodium bicarbonate solution and the separated oil was extracted with dichloromethane. The extract was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from ethanol to give 8-(4-fluorophenyl)-7-(pyridin-4-yl)pyrazolo[1,5-b][1,2,4]triazine (63 mg).

후처리

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturecooled
  3. extractionthe separated oil was extracted with dichloromethane
  4. washThe extract was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel
  8. customthe obtained oil was crystallized from ethanol

출처 및 근거

ORD 기록
ord-6acfb050726d43f8b3a275686f014fbe
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624931

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