Figure 1: Synthesis of sahaquine and its precursors.

Reagents and conditions: (i) HATU, DIEA, dichloromethane, 1 h, (ii) LiOH, methanol, H2O, 1 h, (iii) O-benzylhydroxylamine, HATU, DIEA, dichloromethane, 2 h, (iv) H2, 10% Pd/C, methanol, 4 h. All reactions were performed at room temperature. Yields are shown in brackets. HATU 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, DIEA N,N-diisopropylethylamine, LiOH lithium hydroxide)