ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoate → HCID 60170607, compound

HRID 1817766Notes

Reaction equation

HRID 1817766 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][C:11]([O:13]CC)=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C([O-])=O.[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([C@@H:35]([NH2+:37][NH2:38])[CH3:36])=[CH:31][CH:30]=1)=[O:28])[CH3:25]>C(#N)C>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH2:10][C:11](=[O:13])[N:37]([C@H:35]([C:32]3[CH:33]=[CH:34][C:29]([C:27]([O:26][CH2:24][CH3:25])=[O:28])=[CH:30][CH:31]=3)[CH3:36])[N:38]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 2758177ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoateHCID 86602022HCID 86602022, compound

Product 1

HCID 60170607HCID 60170607, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoate (4.2 g, 16.1 mmol) and {(1S)-1-[4-(ethoxycarbonyl)phenyl]ethyl}hydrazinium trifluoroacetate (5.2 g, 16.1 mmol) were heated in dry acetonitrile (100 ml) to 85° C. for 1 hr. The solvent was removed under reduced pressure, and the residue purified by column chromatography (SiO2, 20% ethyl acetate in hexanes) to give ethyl 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]ethyl}benzoate as a white solid. NMR (500 MHz, CDCl3) δ: 1.38 (t, J=7.1 Hz, 3H); 1.78 (d, J=7.0 Hz, 3H); 3.55 (d, J 22.6 Hz, 1H); 3.60 (d, J=22.6 Hz, 1H); 4.36 (q, J=7.1 Hz, 2H); 5.57 (q, J=7.0 Hz, 1H); 7.39 (t, J=1.9 Hz, 1H); 7.50 (d, J=8.4 Hz, 2H). 7.52 (d, J=1.9 Hz, 2H); 8.02 (d, J=8.4 Hz, 2H). MS C20H18Cl2N2O3 Cald: 404.07; Obsd (M+1): 405.20.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by column chromatography (SiO2, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8eee37187fad46df9d5aef06608c6853
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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