Hydrochloric Acid → 1-(6-Methoxy-3-pyridazinyl)-5-(2-pyridyl)pyrazole-3-carboxylic acid

HRID 1437285Notes

Reaction equation

HRID 1437285 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:7]([C:16]2[N:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[N:6]=1)=[O:4].Cl.C(Cl)(Cl)Cl.CO>CO.O1CCCC1.[OH-].[Na+]>[CH3:23][O:22][C:19]1[N:18]=[N:17][C:16]([N:7]2[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)=[CH:9][C:5]([C:3]([OH:4])=[O:2])=[N:6]2)=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21584188Chloroform methanolHCID 23143541methyl 1-(6-methoxy-3-pyridazinyl)-5-(2-pyridyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 116737881-(6-Methoxy-3-pyridazinyl)-5-(2-pyridyl)pyrazole-3-carboxylic acidYield 67.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-(6-Methoxy-3-pyridazinyl)-5-(2-pyridyl)pyrazole-3-carboxylic acid methyl ester (2.20 g) obtained in Method B step 3) of Referential Example 139 was dissolved in a solvent mixture of methanol (30 mL) and tetrahydrofuran (30 mL), and 1N aqueous sodium hydroxide (15 mL) was added to the solution at room temperature, followed by stirring for 2.5 hours. Under cooling with ice, 1N aqueous hydrochloric acid (15 mL) and a solvent mixture of chloroform-methanol (10:1) were added to the reaction mixture for partitioning the mixture. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and isopropyl ether was added to the residue, and then the precipitated solid was recovered by filtration, to thereby give the title compound (1.42 g, 47.6%).

Workup

  1. additionwas added to the solution at room temperature
  2. additionwere added to the reaction mixture
  3. customfor partitioning the mixture
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was removed under reduced pressure, and isopropyl ether
  7. additionwas added to the residue
  8. filtrationthe precipitated solid was recovered by filtration

Sources & evidence

ORD record
ord-c4530ea073ba483d8338032c3e978d1e
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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