75815-53-1

Upstream product

• 100-39-0 benzyl bromide 
• 51605-32-4 Ethyl 5-Methyl-4-imidazolecarboxylate 
• 51605-32-4 ethyl 4⁽⁵⁾-methylimidazole-5⁽⁴⁾-carboxylate 

Downstream Products

• 75815-55-3 5-methyl-1-(phenylmethyl)-1H-imidazole-4-methanol 
• 108418-73-1 5-methyl-1-(phenylmethyl)-1H-imidazole-4-carboxamide 
• 120231-11-0 1-<5-methyl-1-(phenylmethyl)-1H-imidazol-4-yl>propan-2-one 
• 120231-13-2 α-amino-α,5-dimethyl-1-(phenylmethyl)-1H-imidazole-4-propanoic acid 
• 120231-09-6 1-<5-methyl-1-(phenylmethyl)-1H-imidazol-4-yl>-2-nitropropene 
• 120231-12-1 1-<5-methyl-1-(phenylmethyl)-1H-imidazol-4-yl>propan-2-one oxime 
• 120231-06-3 2-<5-methyl-1-(phenylmethyl)-1H-imidazol-4-yl>-1-nitroethene 
• 120231-07-4 2-<5-methyl-1-(phenylmethyl)-1H-imidazol-4-yl>ethanone oxime 
• 120231-08-5 2-<5-methyl-1-(phenylmethyl)-1H-imidazol-4-yl>ethanamine 
• 75815-57-5 5-methyl-1-(phenylmethyl)-1H-imidazole-4-carboxaldehyde 
• 36376-47-3 2-<5-methyl-1H-imidazol-4-yl>ethanamine dihydrochloride 
• 108418-74-2 7,8-dihydro-1-methyl-8-oxo-6-phenyl-2-(phenylmethyl)imidazo<1,5-a>pyrazinium bromide 
• 108418-75-3 5,6-dihydro-1-methyl-6-phenylimidazo<1,5-a>pyrazin-8(7H)-one 
• 108418-76-4 1-methyl-6-phenylimidazo<1,5-a>pyrazin-8(7H)-one 

Relevant academic research and scientific papers

1H-imidazole derivatives as cannabinoid CB2 receptor modulators

The invention relates to a group of 1H-imidazole derivatives which are modulators of cannabinoid CB2 receptors, to methods for the preparation of these compounds, to novel intermediates useful for the synthesis of said imidazole derivatives, to methods for the preparation of these intermediates, to pharmaceutical compositions containing one or more of these 1H-imidazole derivatives as active ingredient, as well as to the use of these pharmaceutical compositions for the treatment of disorders in which cannabinoid CB2 receptors are involved. The compounds have the general formula (I) wherein R1-R4 have the meanings given in the specification.

Regioselective alkylation of 2-alkyl-5,6,7,8-tetrahydro-3H- cycloheptimidazol-4-ones and 2-alkyl-3H-cycloheptimidazol-4-ones

Regioselective alkylation of 2-alkyl-5,6,7,8-tetrahydro-3H- cycloheptimidazol-4-one (1) and 2-alkyl-3H-cycloheptimidazol-4-one (2) was investigated. 3-[2′-(1-tert-Butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-2- propyl-5,6,7,8-tetrahydro-1H-cycloheptimidazol-4-one (6) was preferentially obtained under the conditions by using NaH in DMF or THF. On the other hand, 3-[2′-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-2-propyl-5,6,7, 8-tetrahydro-3H-cycloheptimidazol-4-one (5), the synthetic intermediate compound of Pratosartan, was obtained selectively in the presence of n-Bu4NBr in toluene by using aqueous sodium hydroxide as a base. In this reaction, it was found that the concentration of the alkaline solution influences its regioselectivity. This selectivity was observed even for aldehyde and ester derivatives.