Synthesis of SR9009 and SR9011

Compounds were synthesized by reductive amination of 5-nitro-2-thiophenecarboxaldehyde with 4-chlorobenzylamine and sodium triacetoxyborohydride yielded the secondary amine. A second reductive amination with 1-Boc-pyrrolidine-3-carboxaldehyde yielded the tertiary amine. This compound was treated with trifluoroacetic acid to remove the Boc-protecting group, and then reacted with either ethyl chloroformate (SR9009) or pentyl isocyanate (SR9011) to give the desired products.

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Solt L.A., Wang Y., Banerjee S., Hughes T., Kojetin D.J., Lundasen T., Shin Y., Liu J., Cameron M.D., Noel R., Yoo S.H., Takahashi J.S., Butler A.A., Kamenecka T.M, & Burris T.P. (2012). Regulation of Circadian Behavior and Metabolism by Synthetic REV-ERB Agonists. Nature, 485(7396), 62-68.

Publication 2012

Amination Amine Boc group Ethyl chloroformate Isocyanate Pyrrolidine Sodium Sr9009 Sr9011 Trifluoroacetic acid

Corresponding Organization : Scripps Research Institute

Other organizations : Howard Hughes Medical Institute, The University of Texas Southwestern Medical Center

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Variable analysis

independent variables

Reductive amination of 5-nitro-2-thiophenecarboxaldehyde with 4-chlorobenzylamine and sodium triacetoxyborohydride
Second reductive amination with 1-Boc-pyrrolidine-3-carboxaldehyde
Treatment with trifluoroacetic acid to remove the Boc-protecting group
Reaction with either ethyl chloroformate (SR9009) or pentyl isocyanate (SR9011)

dependent variables

Formation of the secondary amine
Formation of the tertiary amine
Formation of the desired products (SR9009 or SR9011)

control variables

Sodium triacetoxyborohydride
1-Boc-pyrrolidine-3-carboxaldehyde
Trifluoroacetic acid
Ethyl chloroformate (SR9009)
Pentyl isocyanate (SR9011)

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