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The production process of (3R,4R,5S)-ethyl 4-acetamido-5-(diallylamino)-3-(pyridin-2-yl)-1,2,4-triazepine, also known as compound (3R,4R,5S)-3-(4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl)-4-acetamidobenzoic acid amide (ABX-205), involves a series of chemical reactions and purification steps.
Step 1: Synthesis of (3R,4R)-4-acetamido-3-(pyridin-2-yl)-1,2,4-triazepine
The first step in the production process is the synthesis of (3R,4R)-4-acetamido-3-(pyridin-2-yl)-1,2,4-triazepine, which is done by reacting 3-pyridinecarboxaldehyde with triethylamine and acetic anhydride in the presence of a solvent such as acetonitrile.
This reaction is followed by purification of the resulting product using methods such as flash chromatography or recrystallization.
Step 2: Synthesis of (R)-5-(diallylamino)-3-(pyridin-2-yl)-1,2,4-triazepine
The next step is the synthesis of (R)-5-(diallylamino)-3-(pyridin-2-yl)-1,2,4-triazepine, which is done by reacting (3R,4R)-4-acetamido-3-(pyridin-2-yl)-1,2,4-triazepine with diallyl amine in the presence of a solvent such as dichloromethane.
This reaction is followed by purification of the resulting product using methods such as flash chromatography or recrystallization.
Step 3: Synthesis of (R)-5-(diallylamino)-3-(pyridin-2-yl)-1,2,4-triazepine hydrochloride
The third step is the synthesis of (R)-5-(diallylamino)-3-(pyridin-2-yl)-1,2,4-triazepine hydrochloride, which is done by reacting (R)-5-(diallylamino)-3-(pyridin-2-yl)-1,2,4-triazepine with hydrochloric acid in the presence of a solvent such as ethanol.
This reaction is followed by purification of the resulting product using methods such as recrystallization or precipitation.
Step 4: Synthesis of (3R,4R,5S)-3-(4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl)-4-acetamidobenzoic acid amide (ABX-205)
The final step is the synthesis of (3R,4R,5S)-3-(4,5-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl)-4-acetamidobenzoic acid amide (ABX-205), which is done by reacting (R)-5-(diallylamino)-3-(pyridin-2-yl)-1,2,4-triazepine hydrochloride with 4-acetamidobenzoic acid in the presence of a solvent such as acetonitrile.
This reaction is followed by purification of the resulting product using methods such as flash chromatography or recrystallization.
Challenges and Future Directions
The production process of ABX-205 involves several chemical reactions and purification steps, which can be challenging and time-consuming.
Additionally, the use of hazardous reagents such as hydrochloric acid and acetic anhydride requires careful handling and disposal.
In future