Hydrochloric Acid → 8-(4-Fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine

HRID 54945

반응식

HRID 54945 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.Cl.[N:21]([O-])=O.[Na+].C(=O)(O)[O-].[Na+].[C:30]1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=CC(=O)C)[CH:35]=CC=C[CH:31]=1>O.ClCCl>[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:30]([CH3:35])=[CH:31][N:21]=[N:1][C:2]=23)=[CH:14][CH:15]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 178509114HCID 178509114, 화합물

생성물 1

HCID 229090688-(4-Fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine수율 34.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of 5-amino-4-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazole (100 mg) and concentrated hydrochloric acid (0.2 ml) in water (0.4 ml) was added sodium nitrite (28 mg) in water (0.12 ml) under ice cooling. The mixture was stirred for 30 minutes and to the mixture were added cold dichloromethane (5 ml), an aqueous saturated sodium bicarbonate (2 ml) solution and 1-(triphenylphosphoranylidene)-2-propanone (126 mg) in dichloromethane (2 ml). The mixture was stirred at 10° C. for 2 hours. The organic layer was separated, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from diisopropyl ether to give 8-(4-fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine (41 mg).

후처리

  1. stirringThe mixture was stirred at 10° C. for 2 hours
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel
  6. customthe obtained oil was crystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-f17bbdc8b870482ab97f59b4b5e9954c
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624931

연결된 노트

불러오는 중…