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. Computed Properties of C5H7Cl2N3
Intermediate 20. Step 7: (6R.8aS)-N-((3-chloropyrazin-2-yl)methyl)-2.2-dimethyl-3-oxooctahydroindolizine-6- carboxamide To a solution of (6R,8aS)-2,2-dimethyl-3-oxooctahydroindolizine-6-carboxylic acid (2.9 g, 13.74 mmol) in anhydrous DCM (137 mL) was added isopropyl carbonochloridate (2.02 g, 16.48 mmol) and Epsilon Nu (1.67 g, 16.48 mmol) at 0 C. The reaction mixture was stirred for 1 hour at room temperature. Then Epsilon Nu (2.78 g, 27.47 mmol) and (3-chloropyrazin-2-yl)methanamine hydrochloride (3.2 g, 17.86 mmol) was added , the reaction was stirred for 5 hours at room temperature. The solution was quenched with water, extracted with DCM and the combined organic layer was washed with water, brine and dried over anhydrous Na2SC>4. The organic layer was concentrated in vacuo. The crude was purified by silica gel column chromatography (PE/THF = 3/1) to afford (6R,8aS)-N-((3-chloropyrazin-2-yl)methyl)-2,2-dimethyl-3- oxooctahydroindolizine-6-carboxamide. 1H NMR (400 MHz, CDC13) delta ppm 1.08 – 1.28 (m, 6 H), 1.40 – 1.55 (m, 1 H), 1.70 – 1.91 (m, 2 H), 1.95 – 2.21 (m, 3 H), 2.36 (t, J = 12.4 Hz, 1 H), 2.87 (t, J= 12.4 Hz, 1 H), 3.40 (d, J = 7.6 Hz, 1 H), 4.32 (dd, Ji = 13.2, J2 = 3.2 Hz, 1 H), 4.70 (m, 2 H), 7.05 (s, 1 H), 8.32 (s, 1 H), 8.44 (s, 1 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939412-86-9, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; XU, Jiayi; YU, Wensheng; YU, Younong; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (211 pag.)WO2016/109221; (2016); A1;,
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