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Brodimoprim

Clinical data
ATC code	J01EA02 (WHO)
Identifiers
IUPAC name 5-※pyrimidine-2,4-diamine
CAS Number	56518-41-3
PubChem CID	68760
ChemSpider	62004
UNII	V1YC7T6LLI
KEGG	D07238
ChEBI	CHEBI:131726
ChEMBL	ChEMBL31891
CompTox Dashboard (EPA)	DTXSID20205070
ECHA InfoCard	100.054.745
Chemical and physical data
Formula	C13H15BrN4O2
Molar mass	339.193 g·mol
3D model (JSmol)	Interactive image
Melting point	225——to 228 °C (437——to 442 °F)
SMILES Brc1c(OC)cc(cc1OC)Cc2cnc(nc2N)N
InChI InChI=1S/C13H15BrN4O2/c1-19-9-4-7(5-10(20-2)11(9)14)3-8-6-17-13(16)18-12(8)15/h4-6H,3H2,1-2H3,(H4,15,16,17,18) Key:BFCRRLMMHNLSCP-UHFFFAOYSA-N
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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 ※ (1) with hydroxylamine in PPA gives the——hydroxamide, PC12398304 (2). Further treatment with PPA led to methyl 4-amino-3,5-dimethoxybenzoate ※ (3). Sandmeyer reaction led to Methyl 4-bromo-3,5-dimethoxybenzoate ※ (4). Saponification of the "ester formed 4-Bromo-3,"5-dimethoxybenzoic acid ※ (5). Halogenation with thionyl chloride gave 4-Bromo-3,5-dimethoxybenzoyl chloride ※ (6). Rosenmund reduction gave 4-Bromo-3,5-dimethoxybenzaldehyde ※ (7). {Alternatively DIBAL meant that FGI from ester to aldehyde was accomplished in only 1 step}. Knoevenagel condensation with 3-Methoxypropionitrile ※ (8) afforded ※ (9). Finally, condensation with Guanidine ※ completed the synthesis of Brodimoprim (10).

References※

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