40912-76-3

Upstream product

• 83-40-9 3-methylsalicylic acid 
• 141-78-6 ethyl acetate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 30414-53-0 methyl propanoyl acetate 

Downstream Products

• 337520-48-6 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-methoxycarbonyl-5-methylnitrobenzene 

Relevant academic research and scientific papers

Demonstrating the Synergy of Synthetic, Mechanistic, and Computational Studies in A Regioselective Aniline Synthesis

Tri- and tetrasubstituted anilines are formed in good to excellent yields by the addition of ketones to vinamidinium salts (up to 98%). The reaction proceeds via the formation of dienone intermediates, which react to form an enamine with the liberated amine. In the case of a nitro, or dimethylaminomethylene substituent, the enamines undergo a facile electrocyclic ring closure to form a cyclohexadiene, which goes on to form anilines with a high degree of selectivity (up to 50:1) with a minor competing pathway proceeding via the enol providing phenols. Competition experiments using isotopic substitution reveal that the rate determining step en route to dienone is enol/enolate addition to the vinamidinium salt, which is characterized by an inverse secondary isotope effect (kH/D 0.7-0.9). Computational studies have been used to provide a framework for understanding the reaction pathway. The original proposal for a [1,5]-H shift was ruled out on the basis of the calculations, which did not locate a thermally accessible transition state. The minimum energy conformation of the enamine is such that a facile electrocyclic ring closure is ensured, which is corroborated by the experimental studies. A framework for understanding the reaction pathway is presented.

BENZAMIDINE DERIVATIVES

Benzamidine derivatives of formula (I) or pharmaceutically acceptable salts thereof exhibit excellent inhibitory activity against factor Xa and are useful for treating or preventing blood coagulation disorders: wherein R 1represents a hydrogen atom, a halogen atom, an alkyl group or a hydroxyl group; R 2represents a hydrogen atom, a halogen atom or an alkyl group, R 3represents a hydrogen atom, an optionally substituted alkyl group, an aralkyl group, an optionally substituted alkanoyl group or an optionally substituted alkylsulfonyl group, R 4and R 5 are the same as or different from each other and each represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group or an optionally substituted carbamoyl group, and R 6represents a substituted pyrrolidine group or substituted piperidine group.

Medicaments having psychotropic properties (antitussives)

5-Bromo-N-(N1 -pyrrolidino-alkyl)-ortho-cresotamides having 2 to 5 carbon atoms in the alkyl moiety and therapeutically acceptable salts thereof, compositions containing such compounds useful as antitussives, and a method of suppressing of a cough in a host by administering an effective amount of such a compound with a pharmaceutically acceptable excipient. 5-Bromo-ortho-cresotamide may also be named 5-bromo-2-hydroxy-3-methyl-benzamide.