The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.
Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives
Example 8; A. 1-{3-[2-(1-Methyl-1H-pyrazol-3-ylamino)pyridin-4-yl]-[2,6]naphthyridin-1- yl}piperidine-4-carboxylic acid amide.; 1 -[3-(2-Chloropyridin-4-yl)-[2,6]naphthyridin-1 -yl]-piperidine-4-carboxylic acid amide Example 4A (200 mg, 0.54 mmol), 1 -methyl-1/-/-pyrazol-3-ylamine (110 mg, 1.10 mmol), and cesium carbonate (1.1 g, 3.3 mmol) are dissolved in anhydrous lambda/-methylpyrrolidinone (8.00 ml_) in a dried pressure vessel under argon. The mixture is sparged with argon for 5 min, then palladium(O) tris(tri-f-butylphosphine) (28 mg, 0.05 mmol) is added. The vessel is flushed with argon and sealed, and then heated in a 120 0C oil bath for 5 h. The resulting dark red solution is cooled to rt, then diluted with MeOH and filtered. The filtrate is acidified with several drops of TFA, then purified by preparative reverse-phase HPLC (X-Bridge C18 column, flow rate = 30 mL/min, gradient 10percent–> 80percent acetonitrile/5 mM aqueous trifluoroacetic acid over 30 min). The isolated TFA salt of the product is dissolved in water and basified with 28percent aqueous ammonium hydroxide. The aqueous layer is extracted three times with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulfate, filtered, and concentrated to give the free base. Further purification by preparative reverse-phase HPLC (X-Bridge C18 column, flow rate = 40 mL/min, gradient 10percent –> 80percent acetonitrile/5 mM aqueous ammonium hydroxide over 20 min) afforded the title compound as a white solid (40 mg, 17percent): MS (ESI) m/z 429.4 (M+1 ); 1H NMR (400 MHz, DMSO-d6) delta ppm 9.38 (d, J = 0.76 Hz, 1 H), 9.31 (br s, 1 H), 8.64 (d, J = 5.8 Hz, 1 H), 8.24 (s, 1 H), 8.22 (d, J = 5.3 Hz, 1 H), 8.1 (s, 1 H), 7.87 (d, J = 5.8 Hz, 1 H), 7.53 (d, J = 2.3 Hz, 1 H), 7.42 (dd, J = 5.4, 1.6 Hz, 1 H), 7.34 (br s, 1 H), 6.83 (br s, 1 H), 6.30 (d, J = 2.0 Hz, 1 H), 4.07 (br d, J = 13.4 Hz, 2 H), 3.77 (s, 3 H), 3.10 (m, 2 H), 2.43 (m, 1 H), 1.92 (br m, 4 H).
The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.