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The synthetic routes of 1H-1,2,4-Triazole-3-carboxamide, 5-[[(2-aminoacetyl)amino]methyl]-1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-N,N-dimethyl-, hydrochloride (1:1) are an essential part of the drug discovery and development process in the pharmaceutical industry.
This compound is an important intermediate in the synthesis of antibiotics and anti-inflammatory drugs, and it has a wide range of therapeutic applications.
One of the most common synthetic routes for this compound involves the use of a two-step reaction sequence.
In the first step, 1,3-Bis(2-chloro-4-nitrophenyl)propane is treated with sodium hydroxide to form 1,3-Bis(2-chloro-4-nitrophenyl)amine.
This compound is then reacted with methyl iodide in the presence of a base, such as sodium hydroxide, to form 5-[[(2-aminoacetyl)amino]methyl]-1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-N,N-dimethylamine.
The second step involves the conversion of the amine intermediate into the desired carboxamide.
This is typically accomplished through the use of a carboxylating reagent, such as hydrochloric acid or oxalic acid, in the presence of a solvent, such as ethyl acetate or dichloromethane.
The resulting compound is then hydrolyzed using a strong acid, such as hydrochloric acid or sulfuric acid, to remove the dimethylamide protecting group and form the final product.
Another synthetic route involves the use of a one-pot reaction sequence, which combines both the nucleophilic substitution reaction and the carboxylation reaction into a single step.
This route utilizes a palladium catalyst, such as Pd(OAc)2, and a phosphine ligand, such as 2,2'-bis(diphenylphosphino)acetate, to catalyze the reaction sequence.
The one-pot route begins with the treatment of 1,3-Bis(2-chloro-4-nitrophenyl)propane with sodium hydroxide to form 1,3-Bis(2-chloro-4-nitrophenyl)amine.
This compound is then treated with methyl iodide and the palladium catalyst in the presence of the phosphine ligand and a solvent, such as toluene or xylene, to form the desired carboxamide.
The final product is then hydrolyzed using a strong acid, such as hydrochloric acid or sulfuric acid, to remove the dimethylamide protecting group and form the final product.
Overall, the synthetic routes of 1H-1,2,4-Triazole-3-carboxamide, 5-[[(2-aminoacetyl)amino]methyl]-1-[4-chloro-2-(2-chlorobenzoyl)phenyl]-N,N-dimethyl-, hydrochloride (1:1) are complex and multi-step processes that require careful optimization and control of the reaction conditions.
The selection of a particular synthetic route will depend on the specific requirements of the final product and the cost and availability of the starting materials.