With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.36838-71-8,4-Methylenetetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.
To a solution of N-(3 -(8-ethyl-7-oxo-7, 8-dihydro- 1, 8-naphthyridin-3 -yl)-4-methylphenyl)-2- (trifluoromethyl)isonicotinamide (1 equiv) in DIVIF (0.033 M) was added 4- methylenetetrahydro-2H-pyran (10 equiv). The solution was then irradiated in RPR 200 Rayonet Reactor fitted with 3500A (UVA) lamps over a period of 72 hours. The reaction mixture was evaporated to a solid, dissolved in MeOH and purified by basic reverse phase prep HPLC to give N-(3 -(4-ethyl-3 -oxo-2a,2?,3 ,3 ?,4,5?,6?,8b-octahydro-2H-spiro [cyclobuta[c] [1, 8]naphthyridine- 1 ,4?-pyran] -7-yl)-4-methylphenyl)-2- (trifluoromethyl)isonicotinamide as a white solid in 9% yield. LCMS (m/z) (M+H) = 551.3, Rt = 1.22 mm. ?H NIVIR (400 IVIHz, Methanol-d4) oe 8.90 (d, J= 5.0 Hz, 1H), 8.30 (s, 1H), 8.25 (d, J 2.3 Hz, 1H), 8.12 (dd, J 5.0, 1.3 Hz, 1H), 7.70 -7.62 (m, 2H), 7.52-7.47 (m, 1H), 7.35 (d, J 8.2 Hz, 1H), 4.38-4.18 (m, 2H), 3.77 (dt, J= 11.7, 3.6 Hz, 1H), 3.67-3.54 (m, 2H), 3.53 -3.38 (m, 3H), 3.34-3.32 (m, 1H, overlap with solvent), 2.70-2.59 (m, 1H), 2.31 (s, 3H), 1.93-1.69 (m, 2H), 1.39 (td,J= 12.4, 11.3, 3.7 Hz, 1H), 1.28 (dd,J 13.4, 2.1 Hz, 1H), 1.22 (t, J= 7.0 Hz, 3H)., 36838-71-8
As the paragraph descriping shows that 36838-71-8 is playing an increasingly important role.
Reference£º
Patent; NOVARTIS AG; AVERSA, Robert John; BURGER, Matthew T.; DILLON, Michael Patrick; DINEEN JR., Thomas A.; KARKI, Rajesh; RAMURTHY, Savithri; RAUNIYAR, Vivek; ROBINSON, Richard; SARVER, Patrick James; (374 pag.)WO2017/103824; (2017); A1;,
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