Synthetic Route of 1190380-49-4,Some common heterocyclic compound, 1190380-49-4, name is 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, molecular formula is C8H13N3O, 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.
To a microwave tube was added N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.083 g, 0.24 mmol), 1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine (0.048 g, 0.29 mmol), Pd2(dba)3 (0.022 g, 0.024 mmol), XantPhos (0.028 g, 0.048 mmol), Cs2CO3 (0.16 g, 0.48 mmol) and dioxane (2 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 140 C. for 3 hours and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was dissolved in DMF and purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm¡Á20 mm¡Á2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product as a white solid (26 mg, yield: 25%). 1H NMR (500 MHz, d6-DMSO): delta 10.87 (s, 1H), 8.83 (s, 1H), 8.02 (d, J=5.5 Hz, 1H), 7.97 (s, 1H), 7.60 (d, J=3.0 Hz, 2H), 7.53 (t, J=3 Hz, 1H), 7.43 (s, 1H), 7.24 (s, 1H), 6.77 (d, J=5.0 Hz, 1H), 4.34 (m, 1H), 3.98-3.94 (m, 2H), 3.49-3.45 (m, 2H), 1.95-1.91 (m, 4H). LCMS (ESI) m/z: 432.0 [M+H+].
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, its application will become more common.