Electric Literature of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.
Preparation of 2-[4-(2,3-difluoro-phenoxy)-2-oxo-2H-pyridin-1-yl]-4-methyl-pentanoic acid (1-methyl-1H-pyrazol-3-yl)-amide: A solution of 2-[4-(2,3-difluoro-phenoxy)-2-oxo-2H-pyridin-1-yl]-4-methyl-pentanoic acid (100 mg, 0.3 mmol) in N,N-dimethylformamide (2 mL) at 25¡ã C. was treated with N,N-diisopropyethylamine (0.15 mL, 0.9 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N’N’-tetramethyluronium hexafluorophosphate (HATU) (171 mg, 0.45 mmol) and 1-methyl-1H-pyrazol-3-ylamine (32 mg, 0.33 mmol). The reaction was stirred at 25¡ã C. overnight. At this time, the reaction was diluted with ethyl acetate (30 mL) and was washed with a saturated aqueous ammonium chloride solution (20 mL), a saturated aqueous sodium bicarbonate solution (20 mL) and a saturated aqueous sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, rinsed and concentrated in vacuo. Silica gel column chromatography (100percent ethyl acetate) afforded 2-[4-(2,3-difluoro-phenoxy)-2-oxo-2H-pyridin-1-yl]-4-methyl-pentanoic acid (1-methyl-1H-pyrazol-3-yl)-amide (95 mg, 76percent) as a white solid; ES+-HRMS m/e calcd for C21H22N4O3F2 [M+H+]417.1733, found 417.1733; 1H NMR (400 MHz, DMSO-d6) delta ppm 10.96 (s, 1H), 7.83 (d, J=7.9 Hz, 1H), 7.55 (d, J=2.0 Hz, 1H), 7.40-7.49 (m, 1H), 7.23-7.37 (m, 2H), 6.38 (d, J=2.0 Hz, 1H), 6.22 (dd, J=7.9, 2.8 Hz, 1H), 5.74 (dd, J=11.6, 4.9 Hz, 1H), 5.55 (d, J=2.8 Hz, 1H), 3.74 (s, 3H), 1.97-2.07 (m, 1H), 1.77 (ddd, J=14.2, 9.6, 4.9 Hz, 1H), 1.23-1.37 (m, 1H), 0.88 (d, J=6.6 Hz, 3H), 0.85 (d, J=6.6 Hz, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-pyrazol-3-amine, its application will become more common.