Water → HCID 22909046, compound

HRID 1379023Notes

Reaction equation

HRID 1379023 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](F)[CH:18]=3)=[C:11]3[N:12]=[N:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.O.[C:30](=O)(O)[O-:31].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([O:31][CH3:30])[CH:18]=3)=[C:11]3[N:12]=[N:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22909045HCID 22909045, compound

Product 1

HCID 22909046HCID 22909046, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7-(4-fluorophenyl)-8-(2-fluoropyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine (350 mg) in methanol (2 ml) was added conc. sulfuric acid (0.32 ml) dropwise. The mixture was refluxed for 1 hour, cooled and poured into cold water. The aqueous solution was neutralized with 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 methanol to give 7-(4-fluorophenyl)-8-(2-methoxypyridin-4-yl)pyrazolo[5,1-c][1,2,4]triazine (220 mg).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  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 methanol

Sources & evidence

ORD record
ord-f6641ee69c3247b2a9a3a18742ffaefc
Source dataset
uspto-grants-1997_09
Patent number
US05670503

Reaction notes

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