Scheme 11.
(i) MeOH, SOCl2, reflux; (ii) H2, Pd/C, THF, AcOH, 88% (2 steps); (iii) conc HCl, EtOH, BrCH(CHO)2, 18%; (iv) aq. H2SO4, heat; (v) EDC, HOBt, DMF, 50 °C; (vi) H2NCH2CH2NH2, aq. HCl, reflux, 70%; (vii) Et3N·HCO2H, MeCN, 99%.
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