Tetrahydrofuran → HCID 23090330, compound

HRID 1437283Notes

Reaction equation

HRID 1437283 reaction equation
[OH-:1].[Na+].C(O[C:6]([C:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=2)[N:10]([C:21]2[N:22]=[N:23][C:24](Cl)=[CH:25][CH:26]=2)[N:9]=1)=[O:7])C.[O:28]1[CH2:32]CCC1>CO>[CH3:32][O:28][C:24]1[N:23]=[N:22][C:21]([N:10]2[C:11]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=3)=[CH:12][C:8]([C:6]([OH:7])=[O:1])=[N:9]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86605438HCID 86605438, compound

Product 1

HCID 23090330HCID 23090330, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous 1N sodium hydroxide (14 mL) was added to the above-obtained 1-(6-chloro-3-pyridazinyl)-5-(4-methoxy-2-pyridyl)pyrazole-3-carboxylic acid ethyl ester (2.01 g) in a mixture of methanol (40 mL) and tetrahydrofuran (40 mL) at room temperature, followed by stirring for 1 hour. The reaction solvent was removed under reduced pressure, and water was added to the residue, and the mixture was washed with chloroform. The aqueous layer was partitioned between acetic acid (20 mL) and a methanol-chloroform (1:5) solvent mixture. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was dissolved in methanol (14 mL). In an argon atmosphere, sodium methoxide (0.332 g) was added to the resultant solution at room temperature, followed by stirring for 3 hours. The mixture was refluxed under heat for 2 hours, and then cooled in air. The reaction mixture was partitioned by use of acetic acid (10 mL), water, and methanol-chloroform (1:10) solvent mixture. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, to thereby give the title compound as a solid (0.626 g, 34%).

Workup

  1. customThe reaction solvent was removed under reduced pressure, and water
  2. additionwas added to the residue
  3. washthe mixture was washed with chloroform
  4. customThe aqueous layer was partitioned between acetic acid (20 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  6. filtrationfollowed by filtration
  7. customThe solvent was removed under reduced pressure
  8. dissolutionthe residue was dissolved in methanol (14 mL)
  9. additionIn an argon atmosphere, sodium methoxide (0.332 g) was added to the resultant solution at room temperature
  10. stirringby stirring for 3 hours
  11. temperatureThe mixture was refluxed
  12. temperatureunder heat for 2 hours
  13. temperaturecooled in air
  14. customThe reaction mixture was partitioned by use of acetic acid (10 mL), water, and methanol-chloroform (1:10) solvent mixture
  15. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  16. filtrationfollowed by filtration
  17. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8bb63c5d5af34518b3e8a744b510a0a8
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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