Sodium Hydroxide → 4-[4-(N-cyclohexyl-N-methyl-carbamoyl)-5-propylsulfanylpyrazol-1-yl]benzoic acid

HRID 1799362Notes

Reaction equation

HRID 1799362 reaction equation
[CH:1]1([N:7]([CH3:29])[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([N:7]([CH3:29])[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 59516065Methyl 4-[4-(N-cyclohexyl-N-methyl-carbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate2×

Product 1

HCID 250055804-[4-(N-cyclohexyl-N-methyl-carbamoyl)-5-propylsulfanylpyrazol-1-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[4-(cyclohexyl-methyl-carbamoyl)-5-propylsulfanyl-pyrazol-1-yl]benzoate (Intermediate #4) (162 mg, 0.39 mmol) was dissolved in methanol (10 mL) and treated at ambient temperature with 2M aqueous sodium hydroxide solution (0.96 mL, 1.95 mmol). The mixture was stirred at ambient for 18 h. Methanol was removed by evaporation under reduced pressure and the clear solution diluted with water (25 ml). 2M HCl was added to pH4 and the mixture extracted with ethyl acetate (2×25 mL). The combined extracts were washed with water (2×10 mL) and brine (10 mL), dried (MgSO4) and evaporated to give the title compound as a white solid foam (150 mg, 96%).

Workup

  1. customMethanol was removed by evaporation under reduced pressure
  2. additionthe clear solution diluted with water (25 ml)
  3. addition2M HCl was added to pH4
  4. extractionthe mixture 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. customevaporated

Sources & evidence

ORD record
ord-58abea04c49847b393b1945bc9b6369c
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

Loading…