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. Author manuscript; available in PMC: 2018 Apr 28.
Published in final edited form as: J Med Chem. 2017 Apr 12;60(8):3451–3471. doi: 10.1021/acs.jmedchem.7b00295

Scheme 2. Synthesis of Amide Analoguesa.

Scheme 2

aReagents and conditions: (a) Ac2O, cat. DMAP, pyridine; (b) SOCl2, benzene, 80 °C, then NH3; (c) HATU, TEA, nbutylamine, DCM; (d) HATU, TEA, pyrrolidine, DCM; (e) NaH, MeI, THF; (f) ClSO3H, pyridine, 50 °C, ion exchange using Na+-Dowex resin; (g) HATU, TEA, 2-amino-2-methyl-propanol, DCM.