With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.
Mix an aliquot (1 niL) of a 0.25 M solution of (S)-[l-(6-fluoropyridin-3-yl)- pyrrolidin-3-yl] -amine (0.25 mmol) in toluene, an aliquot (1 mL) of a 1.0 M solution of benzo [delta]thiophene-3-carboxaldehyde (1.0 mmol) in toluene and add a single activated 4A molecular sieve. Stir the reactants at room temperature in air. After 16 h add PS- Trisamine (1.5 mmol) and another single activated 4A molecular sieve. Stir the reactants at room temperature in air. After 24 h filter the reaction solution to remove the PS- Trisamine, and add an aliquot (2 mL) of a 0.25 M solution of sodium borohydride (0.5 mmol) in ethanol. Stir the reactants at room temperature in air. After 48 h add methanol (2 mL) to the reactants and agitate vigorously. Remove the excess reactants by ion- exchange chromatography using a 5g SCX-2 cartridge (0.5 mmol/g SO3H) by wetting it with one column volume of methanol. Apply the mixture to the cartridge and allow it to percolate through the stationary phase (under gravity) into a vial. Wash the cartridge with one column volume of methanol such that these washings also pass into the vial. Replace with a second vial and elute with 3.5N ammonia in methanol (10 mL). Evaporate the solvents from the ammonia washings on a heating block under a stream of nitrogen to give the title compound. 1H NMR (400 MHz, DMSOd6) delta 7.90-7.98 (2H, m)5 7.57 (IH, s), 7.39-7.42 (IH, m), 7.35-7.39 (2H, m), 7.08-7.13 (IH5 m), 6.96 (IH5 dd, J = 8.93, 3.30 ‘ Hz), 4.01 (2H5 S)5 3.43-3.50 (2H5 m), 3.20-3.27 (IH5 m), 3.17 (IH5 d, J = 5.14 Hz)5 3.07- 3.13 (IH5 m), 2.10-2.18 (IH5 m), 1.87-1.95 (IH5 m), MS (ES): m/z = 328 [M+H].
The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; ELI LILLY AND COMPANY; WO2006/44454; (2006); A1;,
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