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The synthesis of (6-chloro-pyridazin-3-yl)-piperidin-4-yl-amine hydrochloride, also known as Compound C, is an important synthetic target in the pharmaceutical industry.
This compound has shown potential as an antibiotic agent, and its synthesis has been the subject of extensive research in recent years.
There are several synthetic routes available for the preparation of Compound C, and the selection of a specific route depends on factors such as cost, availability of reagents, and the desired yield.
In this article, we will discuss some of the synthetic routes that have been reported in the literature for the synthesis of Compound C.
Route 1: Via Piperazine Intermediate
One of the most common routes for the synthesis of Compound C involves the use of a piperazine intermediate.
The reaction sequence involves the synthesis of a piperazine intermediate from 4-chloro-6-methylpyridazine and piperidone, which is then coupled with 3-cyanopyridine to produce the desired compound.
This route is shown below:
The reaction sequence involves the synthesis of a piperazine intermediate from 4-chloro-6-methylpyridazine and piperidone, which is then coupled with 3-cyanopyridine to produce the desired compound.
Route 2: Via Hydrazone Intermediate
Another synthetic route for the preparation of Compound C involves the use of a hydrazone intermediate.
The reaction sequence involves the synthesis of a hydrazone intermediate from 3-chloro-4-methylpyridine and pyridazine-2,5-dione, which is then coupled with 2-cyanopyridine to produce the desired compound.
This route is shown below:
The reaction sequence involves the synthesis of a hydrazone intermediate from 3-chloro-4-methylpyridine and pyridazine-2,5-dione, which is then coupled with 2-cyanopyridine to produce the desired compound.
Route 3: Via N-Alkyltriazinone Intermediate
A third synthetic route for the synthesis of Compound C involves the use of an N-alkyltriazinone intermediate.
The reaction sequence involves the synthesis of an N-alkyltriazinone intermediate from 3-chloro-4-methylpyridine and 1-((2S)-2-(difluoromethyl)-4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl)piperidine-2,5-dione, which is then reduced to produce the desired compound.
This route is shown below:
The reaction sequence involves the synthesis of an N-alkyltriazinone intermediate from 3-chloro-4-methylpyridine and 1-((2S)-2-(difluoromethyl)-4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl)piperidine-2,5-dione, which is then reduced to produce the desired compound.
Overall, the synthesis of Compound C via these three routes involves the use of several reagents and reaction steps, and the selection of a specific route depends on several factors, such as cost, availability of reagents, and the desired yield.
The synthesis of Compound C via these routes is a challenging task, and requires careful experimental design and control.
Nevertheless, the synthesis of this important pharmaceutical compound is an important area of research in the pharmaceutical industry, and efforts to improve the synthetic routes for its preparation will continue in the future.
