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

HRID 1641448노트

반응식

HRID 1641448 반응식
[O-]S(OOS([O-])(=O)=O)(=O)=O.[K+].[K+].S(=O)(=O)(O)O.CN(C)C=O.[Br:23][C:24]1[CH2:28][CH:27]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[C:39](=[O:46])[NH:40][CH:41]([CH:43]2[CH2:45][CH2:44]2)[CH3:42])=[O:30])[N:26]([C:47]2[C:52]([Cl:53])=[CH:51][CH:50]=[CH:49][N:48]=2)[N:25]=1>O>[Br:23][C:24]1[CH:28]=[C:27]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[C:39](=[O:46])[NH:40][CH:41]([CH:43]2[CH2:45][CH2:44]2)[CH3:42])=[O:30])[N:26]([C:47]2[C:52]([Cl:53])=[CH:51][CH:50]=[CH:49][N:48]=2)[N:25]=1

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 24412Potassium PersulfateHCID 441856063-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide

생성물 1

HCID 667361933-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide수율 90.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

0.24 g of potassium peroxodisulfate and 0.02 g of sulfuric acid were added to a N,N-dimethylformamide 3 ml solution comprising 0.10 g of 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide, followed by reflux with heating. 1.5 hours later, the reaction liquid was stood to cool and poured to 10 ml of 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 1/2) to obtain 0.09 g of the desired product.

후처리

  1. temperatureby reflux
  2. temperaturewith heating
  3. custom1.5 hours later, 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 anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/2)

출처 및 근거

ORD 기록
ord-38d77f279aba41a08a51d70af16fb31e
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08115006B2

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