Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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. COA of Formula: C16H19NO2
To a cooled (-35 C) solution of 4-Fluoro-3-nitrobenzenesulfonyl chloride (4.89 g, 20.42 mmol) in THF (50 mL) was added Triethylamine (3.13 mL, 22.46 mmol), followed by addition of Bis-(4-methoxybenzyl)amine (4.97 mL, 20.7 mmol) in THF (50 mL) solution over 30 min. while the temperature was kept at -35 C. After completion of the addition, the temperature was allowed slowly to warm to 0 C over 1 h., and the mixture was stirred at 0 C for an additional hour. The mixture was neutralized with 1 N HC1 to pH about 4-5 and diluted with EtOAc (100 mL). The organic layer was separated, washed with 1 N HC1 (10 mL), 7.5% NaHC03 aqueous solution (20 mL), and brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was treated with DCM (30 mL), and hexane was added to the suspension until it became cloudy. The resulting suspension was sonicated for 2 min. and left at r.t. for 1 h. The mixture was filtered and washed with hexane to afford the desired title product (6.85 g) without further purification. The mother liquid was concentrated under reduced pressure. The residue was treated with DCM (5 mL) and hexane was added as the procedures mentioned above to afford the additional 0.51 g of the title product. Total product 4-fluoro-N,N-bis[(4-methoxyphenyl)methyl]-3-nitro-benzenesulfonamide obtained is 7.36 g (78%). NMR (400 MHz, DMSO-de): d 8.18-8.23 (m, 2 H), 7.75-7.79 (q, 1 H), 7.08 (d, 4 H), 6.81 (d, 4 H), 4.31 (s, 4 H), 3.71 (s, 6 H). 19F NMR (376 MHz, DMSO-d6): d -112.54 (s, 1 F). LCMS calculated for C22H22FN2O6S (M+H)+: m/z = 461.11; found: 461.1.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17061-62-0, its application will become more common.
Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; ZHUO, Jincong; LEAL, Raul; SHETTY, Rupa; LUENGO, Juan; COMBS, Andrew, Paul; (525 pag.)WO2020/97577; (2020); A1;,
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