ORGN 483 |
| In the synthesis of phosphoenolpyruvate carboxykinase (PEPCK) inhibitors for treatment of diabetes, a reductive amination reaction was performed. Thus, the reaction of substituted benzaldehyde and 2-ethyl-2H-pyrazol-3-ylamine under the condition of sodium triacetoxyborohydride and catalytic amount of acetic acid and methylene chloride as solvent yielded desired product, substituted benzyl-(2-ethyl-2H-pyrazol-3-yl)-amine, and a undesired byproduct. To study the mechanism of the side reaction, the byproduct was isolated by reverse phase HPLC. The structure was characterized by various spectroscopic methods. The byproduct was identified as bis-(5-amino-1-ethyl-1H-pyrazol-3-yl)-methyl-phenyl moiety, which indicates the carbon-carbon bond formation between the aldehyde and the amine. |
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New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |