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

HRID 2041062ノート

反応式

HRID 2041062 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-3b3407db84574f09a23ef407c55fed55
出典データセット
uspto-grants-2013_11
特許番号
US08580838B2

反応ノート

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