Brodimoprim

Base Information

• Chemical Name: Brodimoprim
• CAS No.: 56518-41-3
• Molecular Formula: C13H15BrN4O2.
• Molecular Weight: 339.192
• Hs Code.: 2933599090
• European Community (EC) Number: 260-238-8
• UNII: V1YC7T6LLI
• DSSTox Substance ID: DTXSID20205070
• Nikkaji Number: J12.610A
• Wikipedia: Brodimoprim
• Wikidata: Q4973047
• NCI Thesaurus Code: C73255
• Metabolomics Workbench ID: 154575
• ChEMBL ID: CHEMBL31891
• Mol file: 56518-41-3.mol

Synonyms:2,4-diamino-5-(4-bromo-3,5-dimethoxybenzyl)pyrimidine;brodimoprim;Ro 10-5970;Ro-10-5970

Chemical Property of Brodimoprim

Chemical Property:

• Vapor Pressure: 9.85E-13mmHg at 25°C
• Melting Point: 225-228°
• Refractive Index: 1.645
• Boiling Point: 563.8°Cat760mmHg
• PKA: 7.15(at 25℃)
• Flash Point: 294.7°C
• PSA: 96.28000
• Density: 1.514g/cm³
• LogP: 3.17390
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Sparingly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 338.03784
• Heavy Atom Count: 20
• Complexity: 296

Purity/Quality:

99%, ^*data from raw suppliers

Brodimoprim ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1Br)OC)CC2=CN=C(N=C2N)N
• Description: Brodimoprim, a dihydrofolate reductase inhibitor, was introduced for the treatment of common infections of upper respiratory tract such as sinusitis and exacerbation of chronic bronchitis. It has a broad spectrum of antimicrobial activities against most Gram-positive and -negative pathogens including some bacterial strains that are resistant to amoxicillin, a widely used antibiotic for the indicated infections. Brodimoprim also has a favorable pharmacokinetic profile exemplified by its long half-life and good tissue penetration.
• Uses: A structural derivative of Trimethoprim (T795615). A selective dihydrofolate reductase inhibitor; diaminopyridine antibacterial agent.

Technology Process of Brodimoprim

There total 3 articles about Brodimoprim which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C18H17BrN2O2 + guanidine hydrochloride (50-01-1) → brodimoprim (56518-41-3)

Guidance literature:

guanidine hydrochloride; With potassium tert-butylate; In ethanol; at 20 ℃; for 0.5h; Inert atmosphere;

C₁₈H₁₇BrN₂O₂; In ethanol; for 16h; Inert atmosphere; Reflux;

DOI:10.1021/jacs.7b09281

Reference yield:

4-bromo-3,5-dimethoxybenzaldehyde (31558-40-4) → brodimoprim (56518-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 1 h / 20 °C

2.1: potassium tert-butylate / ethanol / 0.5 h / 20 °C / Inert atmosphere

2.2: 16 h / Inert atmosphere; Reflux

With potassium tert-butylate; In ethanol; dimethyl sulfoxide;

DOI:10.1021/jacs.7b09281

Reference yield:

→ brodimoprim (56518-41-3)

Guidance literature:

DOI:10.1002/hlca.19770600854

upstream raw materials:

4-bromo-3,5-dimethoxybenzaldehyde

guanidine hydrochloride

Downstream raw materials:

3-{3-[2-Bromo-5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-methoxy-phenoxy]-propionylamino}-propionic acid benzyl ester

4-{3-[2-Bromo-5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-methoxy-phenoxy]-propionylamino}-butyric acid benzyl ester

2-{3-[2-Bromo-5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-methoxy-phenoxy]-propyl}-2-ethoxycarbonyl-succinic acid diethyl ester

2-{3-[2-Bromo-5-(2,4-diamino-pyrimidin-5-ylmethyl)-3-methoxy-phenoxy]-propyl}-2-ethoxycarbonyl-pentanedioic acid diethyl ester

Refernces

• 1、 Kompis,Wick. "The synthesis of 4-halogen-substituted analogs of trimethoprim". . p. 3025 - 3034. Retrieved 2007/10/09.