Scheme 1. Synthesis of BAIPT-Based SMNPIs 3−5.
Reagents and conditions: (a) Ammonium formate, 10% Pd−C, H2O, 90 °C, 21 h, and then HCOOH. (b) DMAP, DMA, room temperature, 48 h. (c) N1-(7-chloroquinolin-4-yl)-ethane-1,2-diamine (to provide 10), N1-(7-chloroquinolin-4-yl)-propane-1,3-diamine (to provide 11), N1-(7-chloroquinolin-4-yl)-butane-1,4-diamine (to provide 12), HOBt, EDCl, DMA, room temperature, 24 h. (d) Ethylene diamine, NaSH, DMA, 120 °C, 2 h. (e) Methanesulfonic acid, CH3CN, 70 °C, 0.5 h.