Acylation of 2-amino-4,5-dimethoxyacetophenone (I) with 4-nitrocinnamoyl chloride (II) affords amide (III). Simultaneous double bond hydrogenation and nitro group reduction in (III) with hydrogen and Pd/C leads to aniline (IV). This is finally condensed with 4-nitrophenyl isocyanate (V) in the presence of DMAP to produce the corresponding urea
Fischer esterification of 4,5-dimethoxy-2-nitrobenzoic acid (I) with H2SO4 in EtOH affords the corresponding ethyl ester (II). Subsequent nitro group reduction in (II) by hydrogenation over Pd/C provides amino ester (III) (1). Acylation of (III) with 4-nitrocinnamoyl chloride (IV) furnishes amide (V). Simultaneous double bond hydrogenation and nitro group reduction in (V) with H2 and Pd/C leads to amine (VI). This is finally coupled with 4-nitrophenyl isocyanate (VII) in the presence of DMAP to yield the target diaryl urea derivative (1,2).