Synthetic Route of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.
A mixture of (trans)-6-oxooctahydro-l H-quinolizine-3 -carboxylic acid (520 mg, 2.64 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (570 mg, 3.17 mmol), HATU (1.50 g, 3.95 mmol) and TEA (0.79 g, 7.91 mmol) in DCM (13 mL) was stirred at 25 C overnight. The mixture was quenched with H20 (40 mL) and extracted with DCM (15 mL*3).The combined organic layerswere dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product.The crude product was purified by column chromatography on silica gel eluting with PE / THF (0-60%) to give (trans)- N-((3-chloropyrazin-2-yl)methyl)-6-oxooctahydro-l H-quinolizine-3 -carboxamide (0.7 g, 82.35%) as a light yellow solid. 1H NMR (400MHz, CDC13) delta = 8.53 – 8.41 (m, 1H), 8.33 (d, J=2.5 Hz, 1H), 6.96 (br. s., 1H), 5.08 – 4.88 (m, 1H), 4.73 – 4.61 (m, 2H), 3.40 – 3.26 (m, 1H), 2.72 – 2.57 (m, 1H), 2.47 – 2.28 (m, 3H), 2.12 – 2.00 (m, 2H), 1.89 – 1.77 (m, 4H), 1.73 – 1.62 (m, 1H), 1.58 – 1.47 (m, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Chloropyrazin-2-yl)methanamine hydrochloride, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; KOZLOWSKI, Joseph; YU, Wensheng; ANAND, Rajan; YU, Younong; SELYUTIN, Oleg B.; GAO, Ying-Duo; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/114185; (2014); A1;,
Pyrazine – Wikipedia,
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