2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide

HRID 1641447Notes

Reaction equation

HRID 1641447 reaction equation
[Br:1][C:2]1[CH2:6][CH:5]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[C:17](=[O:24])[NH:18][CH:19]([CH:21]2[CH2:23][CH2:22]2)[CH3:20])=[O:8])[N:4]([C:25]2[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][N:26]=2)[N:3]=1.O1CCOCC1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[C:17](=[O:24])[NH:18][CH:19]([CH:21]2[CH2:23][CH2:22]2)[CH3:20])=[O:8])[N:4]([C:25]2[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][N:26]=2)[N:3]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 441856063-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Product 1

HCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamideYield 25.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.13 g of 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide was added to a 1,4-dioxane 6 ml solution comprising 0.14 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone, followed by reflux with heating for 18 hours. After the reaction liquid was stood to cool, it was poured to water, followed by extraction with ethyl acetate, and the organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The filtrate was distilled under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2 to 7/3) to obtain 33 mg of the desired product (melting point: 231 to 233° C.).

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 18 hours
  3. customAfter the reaction liquid
  4. temperatureto cool
  5. extractionfollowed by extraction with ethyl acetate
  6. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over sodium sulfate
  8. distillationThe filtrate was distilled under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2 to 7/3)

Sources & evidence

ORD record
ord-4894a3e77b9d4451a8f9ccd51b9dc295
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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