91563-72-3

Upstream product

• 74-96-4 ethyl bromide 
• 17318-49-9 methyl 2-(ethylamino)benzoate 
• 394-35-4 methyl 2-fluorobenzoate 
• 109-89-7 diethylamine 
• 18624-52-7 2-diethylaminobenzoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 1313574-53-6 methyl 8-oxo-1,2,3,4-tetraphenylspiro[4.5]deca-1,3,6,9-tetraene-7-carboxylate 
• 1026967-41-8 Diethyl-[2-(1-pyridin-2-ylmethyl-1,4,5,6-tetrahydro-cyclopentaimidazol-2-ylsulfanylmethyl)-phenyl]-amine 
• 1027262-54-9 Diethyl-[2-(1-pyridin-4-yl-1,4,5,6-tetrahydro-cyclopentaimidazol-2-ylsulfanylmethyl)-phenyl]-amine 
• 117323-79-2 Diethyl-[2-(1-pyridin-2-yl-1,4,5,6-tetrahydro-cyclopentaimidazol-2-ylsulfanylmethyl)-phenyl]-amine 
• 117323-02-1 Diethyl-{2-[1-(3-methoxy-pyridin-2-yl)-1H-imidazol-2-ylsulfanylmethyl]-phenyl}-amine 
• 117348-31-9 Diethyl-{2-[1-(3-methyl-pyridin-2-yl)-1H-imidazol-2-ylsulfanylmethyl]-phenyl}-amine 

Relevant academic research and scientific papers

Direct access to anthranilic acid derivatives via CO2 incorporation reaction using arynes

(Chemical Equation Presented) CO2 was found to be directly convertible into anthranilic acid derivatives of great synthetic value through a three-component coupling using arynes and amines. Zwitterions arising from nucleophilic attack of amines to arynes serve as key intermediates in the coupling.

2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6- tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors

Substituted 2-sulfinylimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase. The 4,5-unsubstituted imidazole series 6-11 and the 1,4,5,6-tetrahydrocyclopent[d]imidazole series 12 were found to be potent inhibitors of the acid secretory enzyme H+/K+- ATPase. Structure-activity relationships indicate that the substitution of 2- pyridyl groups at the 1-position of the imidazole moiety combined with (2- aminobenzyl)sulfinyl groups at the 2-position leads to highly active compounds with a favorable chemical stability. Other substitution patterns in the imidazole moiety result in reducing biological activities. 2-[(2- Aminobenzyl)sulfinyl]-1-[2-(3-methylpyridyl)]-1,4,5,6- tetrahydrocyclopent[d]imidazole (12h, T-776) was selected for further development as a potential clinical candidate. Extensive study on the acid degradation of 12h indicates a mechanism of action different from that of omeprazole, the first H+/K+-ATPase inhibitor introduced to the market.

Decomposition of 2-dialkylaminobenzoyl azides to yield isocyanates and 1,1 -dialky lindazol-1-ium-3-olates

Substituted benzoyl azides normally yield the correspondingly substituted isocyanates but when a dialkylated amino group is in the 2-position, in addition to the isocyanate, the 1,1-dialkylated indazol-1-ium-3-olate is produced. The ratio of the two products is very variable depending upon the substitution in the benzene ring. Largest yields of the zwitterionic products were found when there was a substituent in the 3-position regardless of whether the substituent was electron-donating or -withdrawing.