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

HRID 54945

Reaktionsgleichung

Reaktionsgleichung von HRID 54945
[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

Komponenten

8

Edukt 5

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

Produkt 1

HCID 229090688-(4-Fluorophenyl)-4-methyl-7-(pyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazineAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f17bbdc8b870482ab97f59b4b5e9954c
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624931

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