Some common heterocyclic compound, 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, molecular formula is C12H12N2O3, 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. 83-10-3
To a suspension of 2-chloro-4-((7-methoxyquinolin-4-yl)oxy)aniline (190 mg, 0.63 mmol) and l,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-lH-pyrazole-4-carboxylic acid (161 mg, 0.69 mmol) in DCM (6 mL) was added EDCI (145 mg, 0.75 mmol) and HOAT (24mg, 0.17mmol). The reaction was heated to 46 C for 17 hours. Additional 1,5- dimethyl-3-oxo-2-phenyl-2,3-dihydro-lH-pyrazole-4-carboxylic acid (30 mg, 0.13 mmol) and EDCI (24 mg, 0.13 mmol) was added. The reaction was stirred further at 46 C for 5 hours, then cooled to rt, quenched with water (10 mL) and extracted with DCM (10 mL). The organic phase was washed with brine (20 mL x 3), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) = 60/1) to give the title compound as a light pink solid (150 mg, 46%). MS (ESI, pos. ion) m/z: 515.2 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-i): delta 2.72 (s, 3H), 3.35 (s, 3H), 3.94 (s, 3H), 5.76 (s, 1H), 6.56 (d, J = 5.2 Hz, 1H), 7.29 (m, 2H), 7.41 (d, J = 2.5 Hz, 1H), 7.46 (m, 2H), 7.54 (m, 2H), 7.60 (t, J = 7.5 Hz, 2H), 8.19 (d, J = 9.2 Hz, 1H), 8.63 (t, J = 7.0 Hz, 1H), 11.19 (s, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 83-10-3, its application will become more common.