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

HRID 448819Notes

Reaction equation

HRID 448819 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=C(C)C=CC=3S([O-])(=O)=O)[CH2:12]2)=[O:10])=[C:4]([C:34](=[O:41])[NH:35][CH:36]([CH:38]2[CH2:40][CH2:39]2)[CH3:37])[CH:3]=1.[BrH:42].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:42])[CH2:12]2)=[O:10])=[C:4]([C:34](=[O:41])[NH:35][CH:36]([CH:38]2[CH2:40][CH2:39]2)[CH3:37])[CH:3]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 867619335-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylcarbamoyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl4-methylbenzene 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-yl4-methylbenzene sulfonate was dissolved in 0.7 mL of acetic acid, and 0.2 mL of a 47 mass % hydrogen bromide aqueous solution was dropwise added, followed by stirring for about 6 days. After completion of the reaction, ethyl acetate, water and 2 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 180 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-c345506dd7cc41558ea2faf334341c1d
Source dataset
uspto-grants-2013_07
Patent number
US08481744B2

Reaction notes

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