128366-51-8

Upstream product

• 868975-15-9 2-(3-bromo-2-methylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 
• 21900-48-1 3-bromo-2-methylbenzoic acid chloride 
• 76006-33-2 3-bromo-2-methylbenzoic acid 
• 1240244-30-7 C₁₆H₁₇N₃O₂ 
• 1240244-31-8 C₁₇H₂₁N₃O₂ 
• 529-20-4 2-methylphenyl aldehyde 
• 83647-43-2 3-bromo-2-methylbenzyl alcohol 
• 128366-50-7 2-(hydroxymethyl)-6-(1'-methyl-1'-(5''-imidazolyl)methyl)toluene 
• 154148-85-3 2-(((3',4'-dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-(5''-imidazolyl)methyl)toluene 
• 154148-87-5 2-(((3',4'dimethoxyphenyl)methoxy)methyl)-6-(1'-oxo-1'-(5''-imidazolyl)methyl)toluene 
• 154148-89-7 2-(((3',4'dimethoxyphenyl)methoxy)methyl)-6-(1'-methylene-1'-(5''-imidazolyl)methyl)toluene 
• 154148-90-0 2-(((3',4'dimethoxyphenyl)methoxy)methyl)-6-(1'-methyl-1'-(5''-imidazolyl)methyl)toluene 
• 154148-88-6 2-(((3',4'dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'methyl-1'-(5''-imidazolyl)methyl)toluene 
• 154148-84-2 2-((3',4'-dimethoxyphenyl)methoxy)methyl-6-bromotoluene 

Downstream Products

• 148324-04-3 C₁₄H₁₆N₂O₂ 
• 148324-04-3 methyl 2-methyl-3-(1'-methyl-1'-(5''-imidazolyl)methyl)benzoate 

Relevant academic research and scientific papers

Pharmaceutical compositions comprising (3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl)methanol

Disclosed herein is a pharmaceutical composition comprising (3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl)methanol and methods of using the composition to treat chronic pain.

4-(1-(3-(HYDROXYMETHYL)-2-METHYLPHENYL)ETHYL)-1H-IMIDAZOLE-2(3H)-THIONE

Disclosed herein is 4-(1-(3-(hydroxymethyl)-2-methylphenyl)ethyl)-1H-imidazole-2(3H)-thione and methods of using the compound to treat chronic pain.

Synthesis of detomidine and medetomidine metabolites: 1,2,3- Trisubstituted arenes with 4'(5')-imidazolylmethyl groups

Two synthetic strategies permitted the synthesis of various metabolites of detomidine (1) and medetomidine (4), potent α-2 adrenoceptor agonists that undergo rapid oxidative metabolism at the aromatic methyl group distal to the imidazole ring. In the detomidine series, the addition of a Grignard reagent prepared from 2-((3',4'-dimethoxyphenyl)methoxy)methyl-6-bromotoluene (13) to imidazole-4(5)-carboxaldehyde (7) provided 2-(((3',4'- dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-(5''- imidazolyl)methyl)toluene (14). In a subsequent reduction, it was possible to differentiate between the secondary benzylic hydroxyl group and the primary benzylic hydroxyl group protected as a 3,4-dimethoxybenzyl ether. Removal of the protecting group provided 3-(hydroxymethyl)detomidine (3-HD) (2) and an oxidation furnished 3-carboxydetomidine (3-CD) (3). However, in the medetomidine series, a similar hydrogenolysis of 2-(((3',4'- dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-methyl-1'-(5''- imidazolyl)methyl)toluene (17) failed, and an alternate, longer route involving dehydration and reduction was necessary to secure 3- (hydroxymethyl)medetomidine (3-HM) (5) and following an oxidation, 3- carboxymedetomidine (3-CM) (6). Finally, an expeditious route to 3-CM (6) involved the addition of the Grignard reagent prepared from 2-(3-bromo-2- methylphenyl)-4,4-dimethyl-2-oxazoline (22) to 4-acetyl-1H-imidazole and the hydrogenolysis and hydrolysis of 2-(1-(4,4-dimethyl-2-oxazolyl))-6-(1'-oxo- 1'-(5'-imidazolyl)methyl)toluene (23).