Brodimoprim


Brodimoprim is a structural derivative of trimethoprim. In brodimoprim, the 4-methoxy group of trimethoprim is replaced with a bromine atom.
As trimethoprim, brodimoprim is a selective inhibitor of bacterial dihydrofolate reductase.

Synthesis

The treatment of Dimethyl 2,6-dimethoxybenzene-1,4-dicarboxylate with hydroxylamine in PPA gives the hydroxamide, PC12398304. Further treatment with PPA led to methyl 4-amino-3,5-dimethoxybenzoate . Sandmeyer reaction led to Methyl 4-bromo-3,5-dimethoxybenzoate . Saponification of the ester formed 4-Bromo-3,5-dimethoxybenzoic acid . Halogenation with thionyl chloride gave 4-Bromo-3,5-dimethoxybenzoyl chloride . Rosenmund reduction gave 4-Bromo-3,5-dimethoxybenzaldehyde .. Knoevenagel condensation with 3-Methoxypropionitrile afforded . Finally, condensation with Guanidine completed the synthesis of Brodimoprim.