Hydrogen Peroxide → 3-[5-Amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-1H-pyrazole-4-carbonyl]-benzoic acid

HRID 2041062Notes

Reaction equation

HRID 2041062 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=[O:28])[CH:22]=1.OO.[O-:32]Cl=O.[Na+].[O-]S([O-])=O.[Na+].[Na+]>CC#N>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([C:10](=[O:11])[NH:12][CH:13]3[CH2:15][CH2:14]3)[CH:16]=[CH:17][C:18]=2[CH3:19])[N:5]=[CH:4][C:3]=1[C:20]([C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=1)[C:27]([OH:32])=[O:28])=[O:29]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 112806793-[5-amino-4-(3-formylbenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamideHCID 23668197Sodium Chlorite

Product 1

HCID 582007883-[5-Amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-1H-pyrazole-4-carbonyl]-benzoic acidYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-[5-amino-4-(3-formylbenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide (900 mg) in CH3CN (25 mL) were added NaH2PO4 (55 mg in 2 mL water) and H2O2 (1.3 g, 30% solution in water) followed by the dropwise addition of an aqueous solution of NaClO2 (365 mg) at 10° C. The mixture was stirred at this temperature for 4 h before Na2SO3 was added. Solvent was removed and residue was dissolved in EtOAc, the organic layer was washed with water and brine and concentrated. The crude product was purified by column chromatography on silica gel eluted with EtOAc followed by EtOAC:AcOH=100:1), to provide the desired intermediate as a beige foam (345 mg, 37%).

Workup

  1. additionwas added
  2. customSolvent was removed
  3. dissolutionresidue was dissolved in EtOAc
  4. washthe organic layer was washed with water and brine
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluted with EtOAc

Sources & evidence

ORD record
ord-3b3407db84574f09a23ef407c55fed55
Source dataset
uspto-grants-2013_11
Patent number
US08580838B2

Reaction notes

Loading…