21801-79-6

Basic information

• Product Name: 2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID
• Synonyms: 2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID;BUTTPARK 9\05-56;ASISCHEM C71528;2-a)pyridine-3-carboxylicacid,2-methyl-imidazo(;2-Methylimidazo[1,2-a]pyridine-3-carboxylic acid ,97%;2-Methylimidazoó1,2-a!pyridine-3-carboxylic acid, 97%;3-Carboxy-2-methylimidazo[1,2-a]pyridine;IMidazo[1,2-a]pyridine-3-carboxylic acid, 2-Methyl-
• CAS NO: 21801-79-6
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Product Categories: Carboxylic Acids;Carboxylic Acids;Fused Ring Systems
• Mol File: 21801-79-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 140 °C
• Boiling Point: 170°C
• Appearance: /
• Density: 1.359 g/cm³
• Refractive Index: 1.653
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.55±0.41(Predicted)
• CAS DataBase Reference: 2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID(21801-79-6)
• EPA Substance Registry System: 2-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID(21801-79-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39-22
• HazardClass: IRRITANT
• Hazardous Substances Data: 21801-79-6(Hazardous Substances Data)

Usage

Chemical Properties

Pink solid

InChI:InChI=1/C9H8N2O2/c1-6-8(9(12)13)11-5-3-2-4-7(11)10-6/h2-5H,1H3,(H,12,13)

Upstream product

• 95607-07-1 3-bromo-2-methyl-pyrido[1,2-a]pyrimidin-4-one 
• 504-29-0 2-aminopyridine 
• 943112-78-5 methyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 1693-94-3 2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 
• 2549-19-1 ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate 

Downstream Products

• 21801-89-8 2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1333519-53-1 N-benzyl-N-methyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 478245-46-4 (2-methylimidazo[1,2-a]pyridin-3-yl)(4-morpholino)methanone 
• 135854-51-2 2-methylimidazo[1,2-a]pyridine-3-carbonyl chloride 
• 570361-36-3 (2-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone 
• 352024-12-5 N-benzyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1367714-25-7 C₂₁H₂₂F₂N₄O 
• 903744-27-4 2-methyl-N-phenethylimidazo[1,2-a]pyridine-3-carboxamide 
• 329715-90-4 N-cyclohexyl-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 357160-94-2 N-(4-bromophenyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 477852-38-3 N-(4-chlorophenyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 331638-05-2 2-methyl-N-(3-(trifluoromethyl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide 
• 352560-80-6 N-(4-ethoxyphenyl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 62772-71-8 2-methyl-N-phenylimidazo[1,2-a]pyridine-3-carboxamide 

Relevant articles and documents

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Lead optimization of a novel series of imidazo[1,2-a]pyridine amides leading to a clinical candidate (Q203) as a multi- and extensively-drug- resistant anti-tuberculosis agent

A critical unmet clinical need to combat the global tuberculosis epidemic is the development of potent agents capable of reducing the time of multi-drug-resistant (MDR) and extensively-drug-resistant (XDR) tuberculosis therapy. In this paper, we report on the optimization of imidazo[1,2-a]pyridine amide (IPA) lead compound 1, which led to the design and synthesis of Q203 (50). We found that the amide linker with IPA core is very important for activity against Mycobacterium tuberculosis H37Rv. Linearity and lipophilicity of the amine part in the IPA series play a critical role in improving in vitro and in vivo efficacy and pharmacokinetic profile. The optimized IPAs 49 and 50 showed not only excellent oral bioavailability (80.2% and 90.7%, respectively) with high exposure of the area under curve (AUC) but also displayed significant colony-forming unit (CFU) reduction (1.52 and 3.13 log10 reduction at 10 mg/kg dosing level, respectively) in mouse lung.

Identification of fused bicyclic heterocycles as potent and selective 5-HT2A receptor antagonists for the treatment of insomnia

A series of fused bicyclic heterocycles was identified as potent and selective 5-HT2A receptor antagonists. Optimization of the series resulted in compounds that had improved PK properties, favorable CNS partitioning, good pharmacokinetic properties, and significant improvements on deep sleep (delta power) and sleep consolidation.