D 7175 can be obtained in a 5-step synthesis starting from 2,e-dichloropyridine (I). Compound (I) is nitrated with HNO3/H2SO4 yielding 2,6-dichloro-3-nitropyridine (II). Subsequent reaction with ammonia and benzylamine leads to 2-amino-3-nitro-6-benzylaminopyridine (IV), which is hydrogenated using Raney Nickel as catalyst te the corresponding 3-amino derivative (V), which reacts without isolation with ethyl chloroformiate to D-7175.
2,6-Dichloro-3-nitropyridine (I) reacts with ammonia and p-chlorobenzylamine (III) yielding 2-amino-3-nitro-6-(4-chlorobenzyl)aminopyridine (IV). D-9389 is obtained after hydrogenation and reaction with ethylchloroformate.
D-11208 is obtained in a five step synthesis: 2,6-Dichloro-3-nitropyridine (I) reacts with ammonia to give 2-amino-3-nitro-6-chloropyridine (II). Subsequent condensation with 4-trifluoromethyl benzylamine (III) yields 2-amino-3-nitro-6-(4-trifluoromethyl)aminopyridine (IV). Hydrogenation with Raney Nickel as catalyst and reaction with ethyl chloroformiate yields D-11208.