Sodium Hydroxide → HCID 59516074, compound

HRID 1160504Notes

Reaction equation

HRID 1160504 reaction equation
[CH:1]1([N:7]([CH3:29])[C:8]([C:10]2[CH:11]=[N:12][N:13]([C:18]3[CH:28]=[CH:27][C:21]([C:22]([O:24]CC)=[O:23])=[CH:20][CH:19]=3)[C:14]=2[CH2:15][CH2:16][CH3:17])=[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:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:27][CH:28]=3)[C:14]=2[CH2:15][CH2:16][CH3:17])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59516062HCID 59516062, compound2×

Product 1

HCID 59516074HCID 59516074, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-[4-(cyclohexyl-methyl-carbamoyl)-5-propyl-pyrazol-1-yl]benzoate (Intermediate #23, 105 mg, 0.26 mmol) was dissolved in methanol (10 mL) and treated at ambient temperature with 2M aqueous sodium hydroxide solution (2.5 mL). The mixture was stirred at ambient temperature for 18 h and then methanol was removed by evaporation under reduced pressure. The remaining aqueous solution was acidified with 2M aqueous hydrochloric acid to pH=2. A white solid precipitated out of solution, it was filtered, dried under vacuum and identified as the desired product (96 mg, quantitative reaction).

Workup

  1. custommethanol was removed by evaporation under reduced pressure
  2. customA white solid precipitated out of solution, it
  3. filtrationwas filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-156386eab7c447efba8da6839def76b9
Source dataset
uspto-grants-2010_10
Patent number
US07816391B2

Reaction notes

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