Sodium Hydroxide → HCID 59516074, compound

HRID 1799368Notes

Reaction equation

HRID 1799368 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-4fdfdca1074b4e08b1fc28b11c99a6d4
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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