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. Author manuscript; available in PMC: 2021 May 28.
Published in final edited form as: J Med Chem. 2020 May 6;63(10):5501–5525. doi: 10.1021/acs.jmedchem.0c00442

Scheme 2.

Scheme 2.

Synthesis of 13a-13d.

Reagents and conditions: (a) hydrazine monohydrate, TBTU, TEA, DMF, yield 50%; (b) propionaldehyde or N-Boc-2-aminoacetaldehyde, MgSO4, ethanol, yield 60–70%; (c) NaBH3CN, HCl, methanol, H2O, methyl orange, yield 60–70%; (d) acrylonitrile or methyl acrylate, ethanol, refluxed, yield 40–50%; (e) TFA, DCM, yield 60%.