Methanol → HCID 57940711, compound

HRID 1437299Notes

Reaction equation

HRID 1437299 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[N:13]([C:14]3[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[N:12]=[C:11]([C:22]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])[CH:10]=2)[CH:4]=1)#N.[OH-:30].[Na+].C[OH:33]>O1CCCC1>[CH3:21][O:20][C:17]1[N:16]=[CH:15][C:14]([N:13]2[C:9]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][N:6]=3)[C:1]([OH:33])=[O:30])=[CH:10][C:11]([C:22]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)=[O:23])=[N:12]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57940678HCID 57940678, compound

Product 1

HCID 57940711HCID 57940711, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[5-(4-cyano-2-pyridyl)-1-(6-methoxy-3-pyridyl)pyrazole-3-carbonyl]piperidine (0.418 g) obtained in Example 98 in a mixture of methanol (8.4 mL) and tetrahydrofuran (8.4 mL), 1N aqueous sodium hydroxide (5.38 mL) was added at room temperature. The resultant mixture was stirred at 80° C. for 7 hours, and then cooled in air. The reaction mixture was partitioned between water and chloroform. The aqueous layer was neutralized to pH 6 with 1N aqueous hydrochloric acid. Chloroform was added for partitioning to the aqueous layer. The aqueous layer was further extracted with chloroform. The organic layers were combined and dried over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure, to thereby give the title compound as a solid (0.239 g, 52%).

Workup

  1. additionwas added at room temperature
  2. temperaturecooled in air
  3. customThe reaction mixture was partitioned between water and chloroform
  4. additionChloroform was added
  5. customfor partitioning to the aqueous layer
  6. extractionThe aqueous layer was further extracted with chloroform
  7. dry with materialdried over sodium sulfate anhydrate
  8. filtrationAfter filtration
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-99ab817974274ec2969ab702dbfaf1a4
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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