Sodium Sulfate → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 1641466Notes

Reaction equation

HRID 1641466 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7](=[O:11])SCC)[N:4]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1.[NH2:19][C:20]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:21]=1[C:22]([NH:24][CH:25]([CH:27]1[CH2:29][CH2:28]1)[CH3:26])=[O:23].S([O-])([O-])(=O)=O.[Na+].[Na+].CC(C)([O-])C.[K+]>CS(C)=O.O>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:19][C:20]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:21]=2[C:22](=[O:23])[NH:24][CH:25]([CH:27]2[CH2:29][CH2:28]2)[CH3:26])=[O:11])[N:4]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]=1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 23665647Potassium tert-butoxideHCID 435330962-amino-5-chloro-N-(1-cyclopropylethyl)benzamideHCID 86639909S-ethyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbothioate

Product 1

HCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamideYield 45.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

0.35 g of S-ethyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbothioate and 0.24 g of 2-amino-5-chloro-N-(1-cyclopropylethyl)benzamide were dissolved in 5 ml of dimethyl sulfoxide, and 0.85 g of anhydrous sodium sulfate was added, followed by stirring for 5 minutes. 0.14 g of potassium tert-butoxide was added at room temperature, followed by stirring for 1.5 hours. The reaction liquid was added to water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/1) to obtain 0.24 g of the desired product.

Workup

  1. stirringby stirring for 1.5 hours
  2. customThe reaction liquid
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/1)

Sources & evidence

ORD record
ord-03f86ded675b4afea7a5b6b732205db2
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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