Sodium Hydroxide → HCID 22037302, compound

HRID 1167553Notes

Reaction equation

HRID 1167553 reaction equation
O.O.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][N:13]=[C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:27])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH2:17][CH2:16]3)[C:11]=2[C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[NH:14][N:13]=[C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:27])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH2:17][CH2:16]3)[C:11]=2[C:28]2[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131723412HCID 131723412, compound

Product 1

HCID 22037302HCID 22037302, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A slurry of 4-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-γ-oxo-1-piperazinebutanoic acid, dihydrate (150 mg, 0.31 mmol) from above in methanol (10 mL) was treated with a solution of sodium hydroxide (12 mg, 0.31 mmol) in methanol (2 mL). The reaction was stirred at room temperature for 15 minutes until dissolution was completed. The solvent was removed in vacuo. The residue was treated with tetrahydrofuran and filtered and air dried to give 150 mg (97%) of 4-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-γ-oxo-1-piperazinebutanoic acid, monosodium salt dihydrate as a solid. Anal. Calc'd. for C22H21ClN5O3Na.2H2O: C, 53.07; H, 5.06; N, 14.07. Found: C, 52.81; H, 5.11; N, 13.90.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with tetrahydrofuran
  3. filtrationfiltered
  4. customair dried

Sources & evidence

ORD record
ord-3575b8eb18b14d2dac616b8e06d16dc6
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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