With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.280774-03-0,(1-Isopropylpiperidin-4-yl)methanol,as a common compound, the synthetic route is as follows.
A microwave vial was charged with l-(6-methoxy-5-methylpyridin-3-yl)-4,5,7,8-tetrahydro-lH- oxepino[4,5-c]pyrazol-3-ol (51 mg, 0.185 mmol), (1 -isop ropyl p i per id i n-4-yl)methanol (68 mg, 0.411 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.143 ml_, 0.547 mmol). The vial was sealed and degassed with nitrogen. Anhydrous toluene (2.5 mL) was added to the reaction mixture which was then heated in a microwave at 120 C for 1 h. The reaction mixture was treated with further (1- isopropylpiperidin-4-yl)methanol (50 mg, 0.302 mmol) and 2-(tributylphosphoranylidene)acetonitrile (0.143 mL, 0.547 mmol) and the reaction mixture was heated at 120 C for 1 h. The reaction mixture was concentrated under a stream of nitrogen and the residue was taken up in water (5 mL) and partitioned with EtOAc (5 mL). The aqueous layer was extracted with further EtOAc (3 x 5 mL) and the combined organic layer wsa passed through a hydrophobic frit and concentrated under reduced pressure. The crude product was purified by MDAP (Method A) to give the title compound (15 mg, 17%). LCMS (Method A) : Rt = 0.66 min, MH+ = 415. 1H NMR (400 MHz, MeOD) delta ppm 8.56 (br. s., 1H), 7.95 (br. s., 1H), 7.51 (br. s., 1H), 4.09 (d, J=5 Hz, 2H), 3.99 (s, 3H), 3.80 (dt, J=15, 5 Hz, 4H), 3.50-3.32 (m, 3H), 2.98 (t, J=12 Hz, 2H), 2.81 (t, J=4 Hz, 2H), 2.74-2.60 (m, 3H), 2.23 (s, 3H), 2.07 (d, J=14 Hz, 2H), 1.81-1.59 (m, 2H), 1.33 (d, J=6 Hz, 6H), 280774-03-0
As the paragraph descriping shows that 280774-03-0 is playing an increasingly important role.
Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BAXTER, Andrew; BERTRAND, Sophie Marie; CAMPBELL, Matthew; DOWN, Kenneth David; HAFFNER, Curt Dale; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; MILLER, William Henry; TALBOT, Eric Philippe Andre; TAYLOR, Jonathan Andrew; (325 pag.)WO2018/192864; (2018); A1;,
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