Ethyl Acetate → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide

HRID 448815Notes

Reaction equation

HRID 448815 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[N:15]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=3)[N:14]=[C:13](C3C(S([O-])(=O)=O)=CC=CN=3)[CH2:12]2)=[O:10])=[C:4]([C:33](=[O:40])[NH:34][CH:35]([CH:37]2[CH2:39][CH2:38]2)[CH3:36])[CH:3]=1.C(O)(=O)C.[BrH:45].C(OCC)(=O)C.[OH-].[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[N:15]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=3)[N:14]=[C:13]([Br:45])[CH2:12]2)=[O:10])=[C:4]([C:33](=[O:40])[NH:34][CH:35]([CH:37]2[CH2:39][CH2:38]2)[CH3:36])[CH:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 867619315-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylcarbamoyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl3-pyridine sulfonate

Product 1

HCID 441856063-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

400 mg of 5-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylcarbamoyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl3-pyridine sulfonate was dissolved in 0.7 mL of acetic acid, and 0.4 mL of a 33 mass % hydrogen bromide acetic acid solution was dropwise added, followed by stirring for about 1 hour. After completion of the reaction, ethyl acetate, water and 2.8 mL of 1 N sodium hydroxide were added, followed by stirring and extraction with ethyl acetate. Then, concentration under reduced pressure was carried out to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/2) to obtain 330 mg of the desired product in a paste form.

Workup

  1. additionwere added
  2. stirringby stirring
  3. extractionextraction with ethyl acetate
  4. concentrationThen, concentration under reduced pressure
  5. customto obtain a crude product
  6. customThe crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-8a00d66b41c646d2b63e8df136519c6c
Source dataset
uspto-grants-2013_07
Patent number
US08481744B2

Reaction notes

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