Application 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.
To a solution of (3S,7R,9aS)-3-methyl-4-oxooctahydropyrido[2,l- c][l ,4]oxazine-7-carboxylic acid (55 mg, 0.26 mmol) in anhydrous DCM (1 mL) was added oxalyl dichloride (0.068 mL, 0.77 mmol) in DCM (0.5 mL) at 0C under N2 atmosphere, and followed by 1 drop of DMF. The resulting mixture was stirred at 0C for 2 hrs. The reaction mixture was evaporated, dissolved with DCM (0.5 mL), and added to a solution of (3-chloropyrazin-2-yl)methanamine hydrochloride (56.1 mg, 0.31 mmol), and triethylamine (0.079 mL, 0.57 mmol) in DCM (1 mL), at 0C under N2 atmosphere, and the mixture was stirred for 12 hrs at 15 C.Then the mixture was diluted with DCM (5 mL), and H20 (5 mL). The organic layer was washed with brine (5 mL), dried over Na2S04, evaporated to get the crude product, which was then purified by prep-TLC (PE/THF=1 : 1) to give (3S,7R,9aS)-N-((3-chloropyrazin-2- yl)methyl)-3-methyl-4-oxooctahydropyrido[2, 1 -c] [ 1 ,4]oxazine-7-carboxamide (55 mg, yield: 62.9 %). 1H NMR (400MHz, CDC13) delta = 8.42 (d, J=2.5 Hz, IH), 8.29 (d, J=2.5 Hz, IH), 7.17 (br. s., IH), 4.76 – 4.57 (m, 2H), 4.16 (q, J=6.9 Hz, IH), 3.92 (dd, J=4.1 , 12.2 Hz, IH), 3.74 (dd, J=2.5, 12.0 Hz, IH), 3.37 – 3.25 (m, IH), 2.73 (t, J=12.3 Hz, IH), 2.42 (tt, J=4.0, 1 1.8 Hz, IH), 2.18 – 2.03 (m, 2H), 1.99 – 1.84 (m, IH), 1.79 – 1.68 (m, 2H), 1.44 (d, J=7.0 Hz, 3H).
The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.
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;,
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