HCID 57940617, compound → HCID 57940634, compound

HRID 1437295Notes

Reaction equation

HRID 1437295 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[C:12]([C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([C:25]2[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[N:15]=1)=[O:13])C>CO.[OH-].[Na+]>[CH3:32][O:31][C:28]1[N:27]=[CH:26][C:25]([N:16]2[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:18][C:14]([C:12]([N:7]3[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]3[CH2:5][C:4]([OH:33])=[O:3])=[O:13])=[N:15]2)=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 57940617HCID 57940617, compound

Product 1

HCID 57940634HCID 57940634, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 1-[1-(6-methoxy-3-pyridyl)-5-phenylpyrazole-3-carbonyl]piperidin-2-ylacetic acid ethyl ester (330 mg) obtained in Example 52 in methanol (4 mL), 1M aqueous sodium hydroxide (1.84 mL) was added, and the mixture was stirred for 2 hours at room temperature. The solvent was removed under reduced pressure, and the residue was partitioned between water and ethyl acetate. The aqueous layer was acidified with 1M aqueous hydrochloric acid (2 mL), followed by extraction with ethyl acetate. The thus-obtained organic layer was washed with water and saturated brine and dried over sodium sulfate anhydrate. The resultant mixture was subjected to filtration, and the solvent was removed under reduced pressure, to thereby give the title compound as an amorphous product (311 mg, 98%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe thus-obtained organic layer was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. filtrationThe resultant mixture was subjected to filtration
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6c7266464f3940b48ba5beb1277c2bd5
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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