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. Author manuscript; available in PMC: 2016 Jan 1.
Published in final edited form as: Bioorg Med Chem. 2014 Nov 11;23(1):222–230. doi: 10.1016/j.bmc.2014.11.007

Scheme 2.

Scheme 2

Synthesis of SA4503 ether analogs 7 – 9. Reagents and reaction conditions: (a) BrCH2CH2Br, K2CO3 / HOCH2CH2OH, 120 °C, 4.5 h; (b) Br(CH2)3Br, K2CO3 / HOCH2CH2OH, 120 °C, 4.5 h; (c) 1-(3-phenylpropyl)piperazine, HOBt•H2O / EDC•HCl / 4-methylmorpholine, 0 °C, N2 overnight; (d) LiAlH4 / THF, 0 °C - ambient temperature, 7.5 h.