Sodium Hydroxide → 4-[4-(Cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

HRID 1799365Notes

Reaction equation

HRID 1799365 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][N:13]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[C:14]=2[S:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[N:12][N:13]([C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=3)[C:14]=2[S:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57857095Methyl 4-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate2×

Product 1

HCID 595160924-[4-(Cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[4-(cyclohexylcarbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate (363 mg, 0.94 mmol) (Intermediate #11) was dissolved in methanol (20 mL) and treated at ambient temperature with 2M aqueous sodium hydroxide solution (2.35 mL). The mixture was stirred at ambient temperature for 18 h and then volatiles were removed by evaporation under reduced pressure. The residue was dissolved in water (25 ml) and 2M HCl was added until the pH=4. The mixture was extracted with ethyl acetate (2×25 mL) and the combined extracts were washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and to evaporated to give the title product as a white solid. (300 mg 85%)

Workup

  1. customvolatiles were removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in water (25 ml)
  3. addition2M HCl was added until the pH=4
  4. extractionThe mixture was extracted with ethyl acetate (2×25 mL)
  5. washthe combined extracts were washed with water (2×10 mL) and brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. customto evaporated

Sources & evidence

ORD record
ord-220ce9d6b81a471c9d53d1cb12750653
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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