86347-15-1

Usage

Uses

Used in Pharmaceutical Industry:
(R)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride is used as a selective α2-adrenoceptor agonist for its high affinity and selectivity, with a Ki of 1.08 nM, exhibiting 1620-fold selectivity over α1-adrenoceptor. This makes it a potentially valuable compound in the development of drugs targeting the α2-adrenergic system for various therapeutic applications.
Used in Veterinary Medicine:
In veterinary medicine, (R)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride is used as a sedative and analgesic due to its α2-adrenergic agonist properties. Its ability to induce sedation and provide analgesia can be beneficial in the management of animal patients, particularly in stressful or painful procedures.
Used in Research Applications:
As a selective α2-adrenoceptor agonist, (R)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride is also used in research settings to study the effects and mechanisms of action of α2-adrenergic agonists. This can include investigations into the modulation of neurotransmitter release, effects on blood pressure, and potential applications in the treatment of various disorders.
The specific applications and uses of (R)-4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride are primarily driven by its pharmacological properties as an α2-adrenergic agonist, which can lead to sedation and analgesia. Its high selectivity for the α2-adrenoceptor over the α1-adrenoceptor suggests that it may have fewer side effects compared to less selective agonists, which could be advantageous in both human and veterinary medicine, as well as in research settings.

Biological Activity

medetomidine is a selective α2-adrenoceptor agonist, with ki of 1.08 nm, exhibts 1620-fold selectivity over α1-adrenoceptor.

InChI:InChI=1/C13H16N2.ClH/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13;/h4-8,11H,1-3H3,(H,14,15);1H

Upstream product

• 1021949-47-2 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene 
• 86347-14-0 medetomidine 
• 1421259-21-3 2-bromo-3-(2,3-dimethylphenyl)butanal 
• 3473-63-0 formamidine acetic acid 
• 1421259-20-2 3-(2,3-dimethylphenyl)butanal 
• 1421259-22-4 2-(2,3-dimethylphenyl)-1,3,2-dioxaborolane 
• 576-23-8 2,3-dimethylbromobenzene 
• 60907-88-2 1-(1-chloroethyl)-2,3-dimethylbenzene 
• 49761-82-2 tert-butyl 1H-imidazole-1-carboxylate 
• 5697-44-9 p-tolylsulfonylmethyl isocyanide 

Downstream Products

• 86347-14-0 medetomidine 
• 145108-58-3 (+)-(S)-4-(1-[2,3-dimethylphenyl]ethyl)-1H-imidazole hydrochloride 

Relevant academic research and scientific papers

Preparation method of dexmedetomidine hydrochloride intermediate

The invention provides a preparation method of a dexmedetomidine intermediate. The method comprises the following steps: (1) dissolving Lewis acid in an aprotic organic solvent, cooling to below 10 DEG C, dropwise adding N-Boc-imidazole dissolved in an aprotic organic solvent, controlling the temperature below 10 DEG C, and uniformly mixing; (2) dropwise adding 1-(1-chloroethyl)-2, 3-dimethyl benzene, heating to 0-45 DEG C after dropwise adding until the reaction is complete, adding water or an inorganic acid aqueous solution for quenching, adding an aprotic organic solvent for extraction, and collecting and merging an extracted organic layer; and (3) adding a poor solvent into the organic layer, separating out a product, and drying. According to the preparation method, by optimizing the feed ratio and reaction conditions, side reactions and by-products are remarkably reduced, the production cost is remarkably reduced, the yield is high, the process is stable, and the preparation method is suitable for industrial mass production.

Preparation method of dexmedetomidine hydrochloride

The invention discloses a preparation method of dexmedetomidine hydrochloride. The method comprises the following steps: taking 2,3-dimethyl-chloroethylbenzene as a raw material, and reacting with magnesium to prepare a Grignard reagent; carrying out addition reaction with formaldehyde to obtain 2-(2, 3-dimethylphenyl) propanol, and carrying out oxidizing through potassium dichromate to obtain 2-(2,3-dimethylphenyl) propionaldehyde; then, reacting with a methanol solution of ammonia gas to obtain imine, performing Van Leusen reaction with p-toluenesulfonylmethyl Isocyanide to obtain medetomidine; and finally, performing tartaric acid chiral resolution to obtain the dexmedetomidine hydrochloride. The method is simple in reaction condition, easy to meet and convenient to operate; and the preparation method is safe and reliable, does not involve high-risk reactions such as alkyl lithium dehydrogenation, catalytic hydrogenation and the like in the prior art, is high in safety coefficient,and has important significance in process safety of the chemical industry where safety production is taken as a first gripper and production accidents happen frequently.

NEW PROCESSES FOR PREPARING 4-SUBSTITUTED IMIDAZOLES

There is provided a novel process for the preparation of a compound of formula (I), (Formula (I)). There is also provided novel processes to intermediates of the compound of formula (I), as well as novel intermediates themselves.

PROCESS FOR THE PREPARATION OF MEDETOMIDINE

A process of preparing Medetomidine of Formula (I) or an acid addition salt thereof, which process comprises: (i) reacting 2,3-dimethyl-methylbenzylalcohol with N-trimethylsilylimidazole, and, if desired, converting the Medetomidine to an acid addition salt thereof.

Method for preparing medetomidine and its salts

The invention provides an improved, highly efficient method for preparing Medetomidine, and its salts, in particular its pharmaceutically acceptable salts. The method utilizes the high reactivity of halogenated imidazoles towards transmetalation with Grignard reagents and the subsequent reaction with 2,3-dimethylbenzaldehyde.