Abstract
A mild, high-yielding, and practical protocol for the direct amidation of alkyl cyanoacetates using DBU is presented. This method eliminates the need for activation of cyanoacetic acid and/or high temperatures. It has been applied to the large-scale synthesis of CP-690,550-10 (1), a compound under development for the treatment of autoimmune diseases.
MeSH terms
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Acetates / chemistry*
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Amides / chemistry*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry*
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Catalysis
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Combinatorial Chemistry Techniques
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Immunosuppressive Agents / chemical synthesis*
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Immunosuppressive Agents / chemistry
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Immunosuppressive Agents / pharmacology
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Molecular Structure
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Piperazines / chemistry
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Pyrimidines / chemical synthesis*
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Pyrimidines / chemistry
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Pyrimidines / pharmacology
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Pyrroles / chemical synthesis*
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Pyrroles / chemistry
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Pyrroles / pharmacology
Substances
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Acetates
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Amides
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Bridged Bicyclo Compounds, Heterocyclic
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CP-690,550-10
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Immunosuppressive Agents
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Piperazines
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Pyrimidines
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Pyrroles
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1,8-diazabicyclo(5.4.0)undec-7-ene
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cyanoacetic acid
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triethylenediamine