Some common heterocyclic compound, 854391-95-0, name is Bis(4-methoxybenzyl)amine hydrochloride, molecular formula is C16H20ClNO2, 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. 854391-95-0
A solution of 2-(benzylthio)-5-chloropyrazine (0.916 g, 3.87 mmol) in DCM (15 mL, 233 mmol) was treated with water (1.5 mL) and the resultant suspension was cooled to between -5 and o C. Sulfuryl chloride (2.2 mL, 26.2 mmol) was added and the reaction mixture was stirred for 2 hours maintaining the temperature between -5 and o C. A slurry of ice/water (10 mL) was added and the organic phase was collected. The aqueous phase was extracted with DCM (2 x 10 mL) and the combined organic extracts were dried (MgS04) and concentrated in vacuo to afford crude intermediate 5- chloropyrazine-2-sulfonyl chloride as a pale yellow liquid (1.198 g). (1370) A suspension of bis(4-methoxybenzyl)amine hydrochloride (1.198 g, 4.08 mmol) and TEA (1.2 mL, 8.61 mmol) in DCM (15 mL) at o C was treated with a solution of 5- chloropyrazine-2-sulfonyl chloride (0.824 g, 3.87 mmol) in DCM (5 mL) dropwise. The resultant solution was stirred at o C for 15 minutes and then allowed to warm to room temperature for 16 hours. A saturated aqueous NH4C1 solution (10 mL) was added and the organic phase was collected. The aqueous phase was extracted with DCM (2 x 10 mL) and the combined organic extracts were dried (MgS04) and concentrated in vacuo. The crude product was purified by chromatography on silica gel (24 g column, 0-30% EtOAc/isohexane) to afford the title compound (1.312 g, 77 %) as a white solid. (1371) NMR (CDCI3) delta 8.78 (d, J = 1.4 Hz, lH), 8.46 (d, J = 1.4 Hz, lH), 7.11 – 7.07 (m, 4H), 6-79 – 6.75 (m, 4H), 4-43 (s, 4H), 3-79 (s, 6H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 854391-95-0, its application will become more common.
Reference:
Patent; INFLAZOME LIMITED; COOPER, Matthew; MILLER, David; MACLEOD, Angus; VAN WILTENBURG, Jimmy; THOM, Stephen; ST-GALLAY, Stephen; SHANNON, Jonathan; (352 pag.)WO2019/8025; (2019); A1;,
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