106961-33-5

Basic information

• Product Name: DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE
• Synonyms: DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE;3-(DiMethylaMinoMethyl)-6-Methyl-2-(4-Methylphenyl)iMidazo[1,2-a]pyridine;N,N-dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine;imidazo[1,2-a]pyridin-3-yl);N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)
• CAS NO: 106961-33-5
• Molecular Formula: C₁₈H₂₁N₃
• Molecular Weight: 279.37944
• Product Categories: Amines, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 106961-33-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.07±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.30±0.28(Predicted)
• CAS DataBase Reference: DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE(106961-33-5)
• EPA Substance Registry System: DIMETHYL-(6-METHYL-2-P-TOLYL-IMIDAZO[1,2-A]PYRIDIN-3-YLMETHYL)-AMINE(106961-33-5)

Safety Data

• Hazardous Substances Data: 106961-33-5(Hazardous Substances Data)

Usage

Uses

3-(Dimethylaminomethyl)-6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine is an impurity of Zolpidem (Z650000), a selective non-benzodiazepine GABAA receptor agonist.

Upstream product

• 88965-00-8 6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine 
• 124-40-3 dimethyl amine 
• 887282-93-1 (6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanol 
• 50-00-0 formaldehyd 

Downstream Products

• 1101863-48-2 C₂₀H₂₄N₃O₂⁽¹⁺⁾*Cl^(1-) 
• 768398-03-4 6-methyl-3-cyanomethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine 
• 82626-48-0 N,N,6-trimethyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-acetamide 
• 189005-44-5 6-methyl-2-(4-methylphenyl)-imidazo<1,2-a>pyridine-3-acetic acid 
• 365213-58-7 2-(4-methylphenyl)-6-methylimidazo[1,2-α]pyridine-3-acetamide 
• 106961-34-6 Trimethyl-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-ammonium; iodide 

Relevant articles and documents

KIO4-mediated Selective Hydroxymethylation/Methylenation of Imidazo-Heteroarenes: A Greener Approach

Herein, we report a KIO4-mediated, sustainable and chemoselective approach for the one-pot C(sp2)?H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields.

PROCESS FOR PREPARING ZOLPIDEM AND ITS INTERMEDIATE

The present invention relates to an improved process for the preparation of 6- methyl-2-[4-methylphenyl]imidazo[l,2-a]pyridine-3-N,N-dimethyl acetamide having formula (1). The compound of formula (1) has adopted name "Zolpidem". The present invention also relates to novel intermediate of the formula (2) and a process for its preparation.Wherein R represents methyl, ethyl, propyl, butyl, isopropyl, isobutyl or tertiary butyl group. The novel intermediate of formula (2) is used in preparation of Zolpidem having formula (1). Zolpidem is useful in the treatment of anxiety, sleep disorders and convulsion.

A structure-activity relationship study of the affinity of selected imidazo[1,2-a]pyridine derivatives, congeners of zolpidem, for the ω1-subtype of the benzodiazepine receptor

A series of 6-substituted 2-aryl-N,N-dimethylimidazol [1,2-a]pyridine-3-acetamides, congeners of zolpidem and alpidem, was synthesized and tested in vitro for binding with the benzodiazepine receptor in the competition with 3H-zolpidem as an ω1-selective radioligand. Molecular electrostatic potential (MEP) and the HOMO and LUMO energies were calculated for the compounds by semi-empirical quantum chemistry methods. The lipophilicity parameter of the compounds, expressed as the logarithm of the octanol-water partition coefficient (log P), was calculated; alternatively, standard values of the Hansch hydrophobic substituent constants π were used. In agreement with earlier investigations on the benzodiazepine receptor ligands with a high preference for the ω1-subtype, a quantitative correlation of the biological data with molecular parameters has revealed a significant dependence (r=0.954) of the binding affinity (IC50) on the deepest MEP minimum, in this case associated with the amide carbonyl oxygen atom. The lipophilicity parameters were found to be of lower significance.