Water → {1-[1-(4-Bromo-phenyl)-ethyl]-3,5-diethyl-1H-pyrazol-4-yl}-acetic acid ethyl ester

HRID 1631932Notes

Reaction equation

HRID 1631932 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([C:11](=O)[CH2:12][CH3:13])[C:7](=O)[CH2:8][CH3:9])[CH3:2].O=C(CC)C(C(=O)CC)CC(OC(C)(C)C)=O.[Br:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]([NH:42][NH2:43])[CH3:41])=[CH:36][CH:35]=1.O>CO>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[C:11]([CH2:12][CH3:13])=[N:43][N:42]([CH:40]([C:37]2[CH:38]=[CH:39][C:34]([Br:33])=[CH:35][CH:36]=2)[CH3:41])[C:7]=1[CH2:8][CH3:9])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 12489386[1-(4-Bromo-phenyl)-ethyl]-hydrazineHCID 50988004Ethyl 4-oxo-3-propanoylhexanoateHCID 866311651,1-Dimethylethyl 4-oxo-3-propanoylhexanoate

Product 1

HCID 66707671{1-[1-(4-Bromo-phenyl)-ethyl]-3,5-diethyl-1H-pyrazol-4-yl}-acetic acid ethyl esterYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-oxo-3-propionyl-hexanoic acid ethyl ester (500 mg) (preparation analagous to that of 1,1-dimethylethyl 4-oxo-3-propanoylhexanoate in WO2007/141267) in methanol (20 ml) at room temperature was added [1-(4-bromo-phenyl)-ethyl]-hydrazine (0.75 g). After overnight stirring, water was added and the mixture extracted 3 times with ethyl acetate. The organic layer was separated; washed with water and brine solution, then dried and concentrated to afford 792 mg of the title compound. Retention time HPLC: 1.58 min (Method D), ESI mass spectrum: (Br) [M]+=393/395.

Workup

  1. extractionthe mixture extracted 3 times with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and brine solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b98dad0bbace4ecd99748fe456f93128
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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