These common heterocyclic compound, 486424-37-7, name is 3-Amino-6-bromopyrazine-2-carboxylic acid, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 3-Amino-6-bromopyrazine-2-carboxylic acid
Step 1. Synthesis of tert-butyl (l-(2-(3-amino-6-bromopyrazine-2-carboxamido)pyridin- 3-yl)-4-methylpiperidin-4-yl)carbamate. In a 100 mL round bottom flask equipped with a magnetic stirrer HBTU (2.23 gm, 5.87 mmol), 3-amino-6-bromopyrazine-2-carboxylic acid (1.17 gm, 5.39 mmol), and N-ethyl-N- isopropylpropan-2-amine (1.28 mL, 7.34 mmol) were allowed to stir in DMF (15 ml) for 15 minutes whereupon tert-butyl (l-(2-aminopyridin-3-yl)-4-methylpiperidin-4-yl)carbamate (1.5 gm, 4.9 mmol) was added in one portion. Reaction was allowed to stir for 16hr. Reaction was then poured into DMF and extracted thrice with 50 mL ethyl acetate. Organic extracts were combined and dried with brine followed by anhydrous sodium sulfate. The residue was purified by silica gel using gradient chromotography ethanol – ethyl acetate 0 -10% which yielded pure tert-butyl (l-(2-(3-amino-6-bromopyrazine-2-carboxamido)pyridin-3-yl)-4-methylpiperidin-4- yl)carbamate (1.86 gm, 67.5% yield) upon evaporation of fractions containing the desired product. LC-MS (Acidic method): ret.time= 1.17 min, M+H = 508.3.
The synthetic route of 3-Amino-6-bromopyrazine-2-carboxylic acid has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; LUZZIO, Michael Joseph; PAPILLON, Julien; VISSER, Michael Scott; (213 pag.)WO2016/20864; (2016); A1;,
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