Hydrochloric Acid → 5-(5-(6-acetamidopyridin-2-yl)-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxamide

HRID 522095Notes

Reaction equation

HRID 522095 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:33])=[C:15]([CH:32]=2)[C:16]([NH:18][C:19]2[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:22]=[C:21]([C:30]#[N:31])[CH:20]=2)=[O:17])[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-:35].[K+].[K+].OO.Cl>CS(C)=O.O>[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:33])=[C:15]([CH:32]=2)[C:16]([NH:18][C:19]2[N:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:22]=[C:21]([C:30]([NH2:31])=[O:35])[CH:20]=2)=[O:17])[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide2×HCID 11430Potassium CarbonateHCID 1184971625-(6-acetamidopyridin-2-yl)-2-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)benzamide

Product 1

HCID 1184971135-(5-(6-acetamidopyridin-2-yl)-2-chlorobenzamido)-1-phenyl-1H-pyrazole-3-carboxamideYield 62.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(6-acetamidopyridin-2-yl)-2-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)benzamide (Example 88, 100 mg, 0.22 mmol) in dimethylsulfoxide (3 mL) was added potassium carbonate (60 mg, 0.44 mmol) followed by hydrogen peroxide (30% w/w solution in water, 441 μL, 4.4 mmol) and the reaction was stirred at room temperature for 2.5 hours. Additional hydrogen peroxide was added (882 μL, 8.8 mmol) and the reaction was stirred for 1 hour. The reaction was diluted with water (5 mL) then neutralised with 2M aqueous hydrochloric acid and extracted into ethyl acetate (3×10 mL). The combined organic extracts were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 80% ethyl acetate in heptanes to furnish the title compound as a colourless solid (65 mg, 62%).

Workup

  1. stirringthe reaction was stirred for 1 hour
  2. extractionextracted into ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with 80% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-a49d9333011443328289ddc2e2c29cc0
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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