Brodimoprim
Chemical compound
From Wikipedia, the free encyclopedia
Brodimoprim is a structural derivative of trimethoprim. In brodimoprim, the 4-methoxy group of trimethoprim is replaced with a bromine atom.
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| ECHA InfoCard | 100.054.745 |
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| Formula | C13H15BrN4O2 |
| Molar mass | 339.193 g·mol−1 |
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| Melting point | 225 to 228 °C (437 to 442 °F) |
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As trimethoprim, brodimoprim is a selective inhibitor of bacterial dihydrofolate reductase.[1]
Synthesis
The treatment of Dimethyl 2,6-dimethoxybenzene-1,4-dicarboxylate [16849-68-6] (1) with hydroxylamine in PPA gives the hydroxamide, PC12398304 (2). Further treatment with PPA led to methyl 4-amino-3,5-dimethoxybenzoate [56066-25-2] (3). Sandmeyer reaction led to Methyl 4-bromo-3,5-dimethoxybenzoate [26050-64-6] (4). Saponification of the ester formed 4-Bromo-3,5-dimethoxybenzoic acid [56518-42-4] (5). Halogenation with thionyl chloride gave 4-Bromo-3,5-dimethoxybenzoyl chloride [56518-43-5] (6). Rosenmund reduction gave 4-Bromo-3,5-dimethoxybenzaldehyde [31558-40-4] (7). {Alternatively DIBAL meant that FGI from ester to aldehyde was accomplished in only 1 step}. Knoevenagel condensation with 3-Methoxypropionitrile [110-67-8] (8) afforded [56518-39-9] (9). Finally, condensation with Guanidine [113-00-8] completed the synthesis of Brodimoprim (10).