Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-bromo-, hydrazide

Base Information

• Chemical Name: Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-bromo-, hydrazide
• CAS No.: 474956-06-4
• Molecular Formula: C8H7BrN4O
• Molecular Weight: 255.07100
• Hs Code.: 2933399990
• Mol file: 474956-06-4.mol

Synonyms:6-Bromo-imidazo[1,2-a]pyridine-2-carboxylic acid hydrazide;

Chemical Property of Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-bromo-, hydrazide

Chemical Property:

• PKA: 8.98±0.20(Predicted)
• PSA: 72.42000
• Density: 1.94±0.1 g/cm3(Predicted)
• LogP: 1.79150

Purity/Quality:

99%, ^*data from raw suppliers

6-Bromo-imidazo[1,2-a]pyridine-2-carbohydrazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-bromo-, hydrazide

There total 2 articles about Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-bromo-, hydrazide 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: 82.0%

ethyl 6-bromoimidazo<1,2-a>pyridine-2-carboxylate (67625-37-0) → 6-bromo-imidazo[1,2-a]pyridine-2-carbohydrazide (474956-06-4)

Guidance literature:

With hydrazine hydrate; In ethanol; at 100 ℃; for 13h;

DOI:10.1021/acs.jmedchem.9b01736

Reference yield:

5-bromo-2-pyridylamine (1072-97-5) → 6-bromo-imidazo[1,2-a]pyridine-2-carbohydrazide (474956-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 6 h / 80 °C

2: hydrazine hydrate / ethanol / 6 h / 80 °C

With hydrazine hydrate; In ethanol;

DOI:10.1007/s00044-013-0887-7

Reference yield: 95.0%

3,4,5-trimethoxy-benzaldehyde (86-81-7) + 6-bromo-imidazo[1,2-a]pyridine-2-carbohydrazide (474956-06-4) → 6-Bromo-imidazo[1,2-a]pyridine-2-carboxylic acid [1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-hydrazide

Guidance literature:

In ethanol; Heating;

upstream raw materials:

ethyl 6-bromoimidazo<1,2-a>pyridine-2-carboxylate

5-bromo-2-pyridylamine

Downstream raw materials:

4-(4-methylbenzylideneamino)-5-(6-bromo-imidazo[1,2-a]pyridin-2-yl)-4H-1,2,4-triazole-3-thiol

Refernces

New 6-bromoimidazo[1,2-A]pyridine-2-carbohydrazide derivatives: Synthesis and anticonvulsant studies

10.1007/s00044-013-0887-7

This research presents the synthesis and anticonvulsant evaluation of new 6-bromoimidazo[1,2-a]pyridine-2-carbohydrazide derivatives, which are designed to possess biologically active hydrazone functionality and substituted 1,2,4-triazole moieties. The purpose of the study was to develop novel antiepileptic drugs with improved therapeutic actions and reduced toxicity. The synthesis involved various chemicals such as 5-bromo-2-aminopyridine, ethyl bromopyruvate, hydrazine hydrate, aromatic aldehydes, carbon disulfide, potassium hydroxide, and different alkyl/benzyl halides. The structures of the synthesized compounds were confirmed through spectral techniques like FTIR, 1H NMR, 13C NMR, and mass spectrometry. The in vivo anticonvulsant properties were assessed using maximal electroshock seizure and subcutaneous pentylene tetrazole methods, with toxicity studies performed using the rotarod method. The research concluded that most of the new compounds exhibited significant anticonvulsant properties without toxicity up to 100 mg/kg, with compounds 3b and 4 showing complete protection against seizures, comparable to the standard drug diazepam. These findings suggest that linking imidazo[1,2-a]pyridines with triazole and hydrazone moieties can lead to potent anticonvulsants with minimal side effects.