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

HRID 54945

Reaction equation

HRID 54945 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f17bbdc8b870482ab97f59b4b5e9954c
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Linked notes

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