1021949-47-2

Basic information

• Product Name: 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole
• Synonyms: 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole;5-[1-(2,3-Dimethylphenyl)ethenyl]-1H-imidazole;4-[1-(2,3-DiMethyl-phenyl)-vinyl]-1H-iMidazole;5-(1-(2,3-DiMethylphenyl)vinyl)-1H-iMidazole;Medetomidine Impurity 3;5-[1-(2,3-Dimethylephenyl]-1H-imidazole
• CAS NO: 1021949-47-2
• Molecular Formula: C₁₃H₁₄N₂
• Molecular Weight: 198
• Mol File: 1021949-47-2.mol

Chemical Properties

• Boiling Point: 393.2±11.0 °C(Predicted)
• Appearance: /
• Density: 1.066
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.68±0.10(Predicted)
• CAS DataBase Reference: 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole(1021949-47-2)
• EPA Substance Registry System: 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole(1021949-47-2)

Safety Data

• Hazardous Substances Data: 1021949-47-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole is used as an impurity in the production of Dexmedetomidine, an α2-Adrenergic agonist. Its presence is significant for the pharmaceutical industry as it may affect the quality, efficacy, and safety of the final drug product. Understanding and controlling the levels of this impurity are crucial for ensuring the therapeutic benefits and minimizing potential side effects of Dexmedetomidine.
Used in Research and Development:
As an impurity in Dexmedetomidine, 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole may be used in research and development to study its potential effects on the pharmacological properties of the parent compound. This could involve investigating its interactions with the α2-Adrenergic receptors, its role in the sedative and analgesic effects of Dexmedetomidine, and its potential impact on the drug's overall safety profile.
Used in Quality Control and Regulatory Compliance:
The presence of 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole as an impurity in Dexmedetomidine necessitates its inclusion in quality control processes and regulatory compliance efforts. This involves developing and validating analytical methods to accurately quantify the levels of this impurity in the final drug product, as well as establishing acceptable limits to ensure the safety and efficacy of the medication.
Used in Drug Synthesis and Process Optimization:
Understanding the role of 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole in the synthesis of Dexmedetomidine can help researchers and chemists optimize the manufacturing process. This may involve identifying ways to minimize the formation of this impurity, improving the overall yield and purity of the final product, and reducing the potential for contamination or degradation during production.
Used in Toxicology and Safety Assessment:
As an impurity in a pharmaceutical product, 5-[1-(2,3-DiMethylphenyl)ethenyl]iMidazole may be subject to toxicological and safety assessments. This involves evaluating its potential toxic effects, determining its safety profile, and establishing guidelines for acceptable exposure levels in the final drug product. These assessments are essential for ensuring the overall safety of Dexmedetomidine and protecting patients from potential adverse effects.

InChI:InChI=1S/C13H14N2/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13/h4-8H,3H2,1-2H3,(H,14,15)

Synthetic route

1-(2,3-dimethylphenyl)-1-(1H-imidazol-4-yl)ethanol → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 0.11℃; for 2h; Reagent/catalyst; Solvent; Temperature; Dean-Stark;	100%

4-(2,3-dimethylbenzoyl)-1H-imidazole + Methyltriphenylphosphonium bromide (1779-49-3) → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20 - 25℃; for 18h; Wittig Olefination;	94%

(1-trityl-1H-imidazol-4-yl)boronic acid + C10H11Br → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Stage #1: (1-trityl-1H-imidazol-4-yl)boronic acid; C10H11Br With tris-(dibenzylideneacetone)dipalladium(0); sodium phosphate In 5,5-dimethyl-1,3-cyclohexadiene; water at 105℃; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran at 20 - 65℃; for 1.5h; Reagent/catalyst; Solvent; Temperature;	74.9%

5-[1-(2,3-dimethylphenyl)vinyl]-1H-imidazole hydrochloride → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
With sodium hydroxide; water at 0 - 25℃; for 1 - 1.5h;

4-<(2,3-dimethylphenyl)carbonyl>-1-(triphenylmethyl)imidazole (176721-02-1) → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 24 h / 0 °C / Inert atmosphere 2.1: trifluoroacetic acid; water / 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 4 h / 20 °C 2.1: hydrogenchloride / dichloromethane View Scheme

4-(1-(2,3-dimethylphenyl)vinyl)-1-trityl-1H-imidazole → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
With water; trifluoroacetic acid at 20℃; for 12h;
With hydrogenchloride In dichloromethane	19.5 g

4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole (176721-01-0) → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: manganese(IV) oxide / 1,4-dioxane / Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.2: 24 h / 0 °C / Inert atmosphere 3.1: trifluoroacetic acid; water / 12 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: manganese(IV) oxide / 1,4-dioxane / 5 h / Reflux 2: tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C 3: triethylsilane; trifluoroacetic acid / dichloromethane / 4 h / -10 °C View Scheme
Multi-step reaction with 3 steps 1.1: manganese(IV) oxide / 1,4-dioxane / 3 h / Reflux 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 2.2: 4 h / 20 °C 3.1: hydrogenchloride / dichloromethane View Scheme

2,3-dimethylbromobenzene (576-23-8) → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: magnesium / tetrahydrofuran 1.2: 0 °C 2.1: manganese(IV) oxide / 1,4-dioxane / Reflux 3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.2: 24 h / 0 °C / Inert atmosphere 4.1: trifluoroacetic acid; water / 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / Reflux 1.2: 1.5 h / 0 - 20 °C 2.1: manganese(IV) oxide / 1,4-dioxane / 5 h / Reflux 3.1: tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C 4.1: triethylsilane; trifluoroacetic acid / dichloromethane / 4 h / -10 °C View Scheme
Multi-step reaction with 4 steps 1.1: (bis(tricyclohexyl)phosphine)palladium(II) dichloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 30 °C / Inert atmosphere 2.1: caesium carbonate / ethanol / 30 °C / Inert atmosphere 3.1: hydrogen bromide; acetic acid / dichloromethane / 0 - 10 °C / Inert atmosphere 4.1: sodium phosphate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene; water / 105 °C / Inert atmosphere 4.2: 1.5 h / 20 - 65 °C View Scheme
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 1.5 h / 70 °C / Inert atmosphere 1.2: -5 - 20 °C / Inert atmosphere 2.1: manganese(IV) oxide / 1,4-dioxane / 3 h / Reflux 3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 3.2: 4 h / 20 °C 4.1: hydrogenchloride / dichloromethane View Scheme
Multi-step reaction with 3 steps 1.1: ethylene dibromide; magnesium / tetrahydrofuran / 1 h / 40 - 65 °C 1.2: 2 h / -5 - 0 °C 1.3: 3 h / 30 °C 2.1: tetrahydrofuran / 2 h / 0.4 - 65 °C / Large scale 3.1: toluene-4-sulfonic acid / toluene / 2 h / 0.11 °C / Dean-Stark View Scheme

(2,3-dimethylphenyl)(1H-imidazol-4-yl)methanol → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Dess-Martin periodane; magnesium sulfate / dichloromethane / 12 h / 20 - 30 °C 2: potassium tert-butylate / tetrahydrofuran / 18 h / 20 - 25 °C View Scheme

2,3-dimethylbenzaldehyde (5779-93-1) → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 35 - 65 °C / Inert atmosphere 1.2: 6 h / 20 - 25 °C 2.1: Dess-Martin periodane; magnesium sulfate / dichloromethane / 12 h / 20 - 30 °C 3.1: potassium tert-butylate / tetrahydrofuran / 18 h / 20 - 25 °C View Scheme

4-<1-(2,3-dimethylphenyl)-1-hydroxyethyl>-1-(triphenylmethyl)imidazole (176721-03-2) → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane at -10℃; for 4h;

trimethylsilyl-2,3-dimethylphenylacetylene → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: caesium carbonate / ethanol / 30 °C / Inert atmosphere 2.1: hydrogen bromide; acetic acid / dichloromethane / 0 - 10 °C / Inert atmosphere 3.1: sodium phosphate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene; water / 105 °C / Inert atmosphere 3.2: 1.5 h / 20 - 65 °C View Scheme

1-ethynyl-2,3-dimethylbenzene (767-87-3) → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen bromide; acetic acid / dichloromethane / 0 - 10 °C / Inert atmosphere 2.1: sodium phosphate; tris-(dibenzylideneacetone)dipalladium(0) / 5,5-dimethyl-1,3-cyclohexadiene; water / 105 °C / Inert atmosphere 2.2: 1.5 h / 20 - 65 °C View Scheme

4-(2,3-dimethylbenzoyl)-1H-imidazole → 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 0.4 - 65 °C / Large scale 2: toluene-4-sulfonic acid / toluene / 2 h / 0.11 °C / Dean-Stark View Scheme

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + trityl chloride (76-83-5) → 4-(1-(2,3-dimethylphenyl)vinyl)-1-trityl-1H-imidazole

Conditions	Yield
With triethylamine In chloroform at 20 - 26℃; for 2h; Inert atmosphere;	100%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + benzyl chloroformate (501-53-1) → benzyl 4-(1-(2,3-dimethylphenyl)vinyl)-1H-imidazole-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 25h; Inert atmosphere;	99.2%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + p-toluenesulfonyl chloride (98-59-9) → 4-(1-(2,3-dimethylphenyl)vinyl)-1-tosyl-1H-imidazole

Conditions	Yield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃; for 2h; Inert atmosphere;	97.6%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 4-(1-(2,3-dimethylphenyl)vinyl)-1H-imidazole-1-carboxylate

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 19h; Inert atmosphere;	96.9%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) → 4-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1H-imidazole hydrochloride

Conditions	Yield
With (1R,1’R,2S,2’S)-2,2’-di-tert-butyl-2,3,2’,3’-tetrahydro-1H,1‘H-(1,1‘)biisophosphindolyl; hydrogenchloride; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen In toluene at 20℃; under 5171.62 Torr; for 10h; Solvent; Pressure;	91.6%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) → (±)-4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole hydrochloride (86347-15-1)

Conditions	Yield
Stage #1: 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene With hydrogen; 5%-palladium/activated carbon In methanol; water at 44 - 46℃; under 1575.16 Torr; for 1.5h; Stage #2: With hydrogenchloride In water at -10 - 42℃; for 2.5 - 3h;	89%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + methanesulfonyl chloride (124-63-0) → 4-(1-(2,3-dimethylphenyl)vinyl)-1-(methanesulfonyl)-1H-imidazole

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	87.7%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) → medetomidine (86347-14-0)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 40℃;	84.6%
With palladium 10% on activated carbon; hydrogen at 10 - 20℃; under 760.051 - 1520.1 Torr;	4.2 g

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + benzyl bromide (100-39-0) → 1-benzyl-4-(1-(2,3-dimethylphenyl)vinyl)-1H-imidazole (1311376-20-1)

Conditions	Yield
Stage #1: 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere;	76.1%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + L-Tartaric acid (87-69-4) → (S)-dexmedetomidine-L-(+)-tartrate (176721-04-3)

Conditions	Yield
Stage #1: 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene With (+)-1,2-bis((2S,5S)-diethylphospholano)benzene(cyclooctadiene)rhodium(I)trifluoromethanesulfonate; hydrogen In ethanol at 40 - 50℃; under 2280.15 - 3040.2 Torr; for 10h; Stage #2: L-Tartaric acid In ethanol at 70 - 80℃; for 0.5h; Solvent; Temperature; Pressure;	76.1%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + dimethylamino sulfonyl chloride (13360-57-1) → 4-(1-(2,3-dimethylphenyl)vinyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Conditions	Yield
With triethylamine In chloroform at 20℃; for 23h; Inert atmosphere;	67.2%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + chloromethyl methyl ether (107-30-2) → 4-(1-(2,3-dimethylphenyl)vinyl)-1-(methoxymethyl)-1H-imidazole

Conditions	Yield
Stage #1: 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene With sodium hydride In N,N-dimethyl-formamide at 4 - 20℃; for 1h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide at 20 - 28℃; for 1.13333h; Inert atmosphere;	63.6%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + acetyl chloride (75-36-5) → 1-(4-(1-(2,3-dimethylphenyl)vinyl)-1H-imidazol-1-yl)ethan-1-one

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	63.1%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 4-(1-(2,3-dimethylphenyl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

Conditions	Yield
Stage #1: 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-d6-formamide at 20℃; for 1h; Inert atmosphere;	53.9%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + O,O'-dibenzoyl-L-tartaric acid (2743-38-6) → C13H16N2*C18H14O8

Conditions	Yield
Stage #1: 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene With bis(norbornadiene)rhodium(l)tetrafluoroborate; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; hydrogen In methanol at 50℃; under 7500.75 Torr; for 22h; Glovebox; Stage #2: O,O'-dibenzoyl-L-tartaric acid In methanol at 20 - 25℃; for 3.75h; Inert atmosphere;	47%

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) → (+/-)-4(5)-<1-(2,3-Dimethylphenyl)ethyl-1H-imidazole> (86347-14-0)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2068.65 Torr; for 8h;	36 mg

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + p-toluenesulfonyl chloride (98-59-9) → 4-(1-(2,3-dimethylphenyl)ethyl)-1-tosyl-1H-imidazole

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; triethylamine / 1,2-dichloro-ethane / 2 h / 20 °C / Inert atmosphere 2: bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene / dichloromethane / 20 h / 10 °C / 6000.6 Torr View Scheme

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl-4-(1-(2,3-dimethylphenyl)ethyl)-1H-imidazole-1-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere 2: bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene / dichloromethane / 18 h / 10 °C / 6000.6 Torr View Scheme

1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene (1021949-47-2) + benzyl chloroformate (501-53-1) → benzyl-4-(1-(2,3-dimethylphenyl)ethyl)-1H-imidazole-1-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 25 h / 20 °C / Inert atmosphere 2: bis(norbornadiene)rhodium(l)tetrafluoroborate; hydrogen; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene / dichloromethane / 18 h / 10 °C / 6000.6 Torr View Scheme

Upstream product

• 767-87-3 1-ethynyl-2,3-dimethylbenzene 
• 176721-03-2 4-<1-(2,3-dimethylphenyl)-1-hydroxyethyl>-1-(triphenylmethyl)imidazole 
• 1900755-49-8 (1-trityl-1H-imidazol-4-yl)boronic acid 
• 5779-93-1 2,3-dimethylbenzaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 576-23-8 2,3-dimethylbromobenzene 
• 176721-01-0 4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole 
• 176721-02-1 4-<(2,3-dimethylphenyl)carbonyl>-1-(triphenylmethyl)imidazole 

Downstream Products

• 86347-15-1 (±)-4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole hydrochloride 
• 86347-14-0 (+/-)-4(5)-<1-(2,3-Dimethylphenyl)ethyl-1H-imidazole> 
• 86347-14-0 medetomidine 
• 176721-04-3 (S)-dexmedetomidine-L-(+)-tartrate 
• 113775-47-6 dexmedetomidine 
• 1311376-20-1 1-benzyl-4-(1-(2,3-dimethylphenyl)vinyl)-1H-imidazole 

Relevant articles and documents

METHOD FOR PREPARING DEXMEDETOMIDINE

The present invention relates to a method for preparing dexmedetomidine having the following formula (I): or a pharmaceutically acceptable salt and/or solvate thereof, comprising the following successive steps: a) asymmetric hydrogenation of a methylene derivative of the following formula (II): in order to obtain dexmedetomidine, and b) optionally salifying and/or solvating dexmedetomidine in order to obtain a pharmaceutically acceptable salt and/or solvate of dexmedetomidine, wherein the methylene derivative of formula (II) is prepared from a halide of the following formula (V), in which Hal2 represents a halogen atom such as Br, and a cyanoimidazole of the following formula (VI):. The present invention relates also to methods for preparing synthesis intermediates of dexmedetomidine from the halide of formula (V) and the cyanoimidazole of formula (VI), these synthesis intermediates being the methylene derivative of formula (II), an alcohol of the following formula (III), and a ketone of the following formula (IV):.

A right-US supporting [...] and its hydrochloride preparation method

Invention provides a right-US supporting [...] and its hydrochloride preparation method. In particular, the invention using carbon-carbon hydrogenation reduction catalyst and (R, S) - Duanphos composition as a catalyst to the double bond of a chiral catalytic reduction, directly by the enantiomeric excess percentage up to 99.9% of the right us holds the onamot to decide, the preparation method of the present invention short synthetic route, the product does not need to chiral separation, high yield.

Preparation method of dexmedetomidine hydrochloride and its intermediate

The invention discloses a preparation method of dexmedetomidine hydrochloride and its intermediate. A preparation method of dexmedetomidine L-tartrate comprises the steps of subjecting dexmedetomidineintermediate III and hydrogen to reduction reaction in an organic solvent in the presence of a chiral catalyst, and subjecting the reduced product and tartaric acid to neutralization reaction to obtain dexmedetomidine L-tartrate II, wherein the chiral catalyst is (+)-1,2-bis(2S-5S)-diethylphospholano-benzene(1,5-cyclooctadiene)rhodium trifluoromethanesulfonate. The preparation method herein has ashort step path, has no need for chiral splitting, and has high total molar yield; the product prepared herein has high purity, reaches the standard for bulk pharmaceutical chemicals and is suitablefor industrial production.

Process method for preparation of dexmedetomidine hydrochloride

The invention provides a synthetic method for dexmedetomidine hydrochloride. The synthetic method is characterized in that the dexmedetomidine hydrochloride is synthesized by using 2,3-dimethyl benzaldehyde and (1-(trimethylsilyl)-1H-imidazole-4-yl)magnesium bromide as starting materials through a reaction. The method adopts Dess-Martin to synthesize a compound III, and uses a Wittig reagent to synthesize a compound IV, so reaction conditions are greatly reduced, and synthetic reaction steps are shortened. The synthetic method provided by the invention has the advantages of simple operation, mild control points, high product purity, and applicability to industrial production.

A novel and facile route for the synthesis of medetomidine as the α2-adrenoceptor agonist

Abstract: We report here a novel and facile method for the synthesis of (±)-4(5)-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole (medetomidine) in a good yield in five steps. The method involves Wittig olefination of the phenylimidazolylketones, followed by a hydrogenation. We demonstrate that the Wittig alkenylation reaction provides a convenient step for the synthesis of medetomidine without requiring methylation and dehydration steps, which are problematic processes in the previous methods. Graphical Abstract: Novel route for the synthesis of medetomidine.[Figure not available: see fulltext.].

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.

Antihypertensive substituted imidazole derivatives

The invention provides novel compounds of the formula: STR1 wherein the various substituents are defined herein below. Processes for the preparation of these compounds are described, as are novel pharmaceutical compositions comprising at least one of the compounds of their salts. The compounds and their non-toxic salts exhibit valuable pharmacological activity and are useful in the treatment of mammals, especially as antihypertensive agents. Furthermore, some of the compounds have proved to possess antithrombotic and diuretic activity. Antimycotic and antifungal properties have also been found.