Hydrogen Peroxide → 5-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxamide

HRID 522093Notes

Reaction equation

HRID 522093 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]#[N:19])[CH:8]=1)=[O:5].C([O-])([O-])=[O:32].[K+].[K+].OO>CS(C)=O.O.Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([F:30])=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=[C:9]([C:18]([NH2:19])=[O:32])[CH:8]=1)=[O:5]

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 1184970562-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-5-(3-fluoropyridin-2-yl)benzamide

Product 1

HCID 1184971615-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxamideYield 51%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-chloro-N-(3-cyano-1-phenyl-1H-pyrazol-5-yl)-5-(3-fluoropyridin-2-yl)benzamide (Example 90, 100 mg, 0.24 mmol) in DMSO (3 mL) was added K2CO3 (66 mg, 0.48 mmol) and H2O2 (30% aqueous solution, 1.5 mL) and the reaction was stirred at room temperature for 18 hours. The reaction was diluted with water (1 mL), and 2M aqueous HCl (3 mL) was added resulting in precipitation of a white solid. The solid was filtered, washed with water and dried to afford the title compound as a colourless solid (52.8 mg, 51%).

Workup

  1. additionwas added
  2. customresulting in precipitation of a white solid
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a1ea63590b414bc8a84056666968bae8
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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