In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5932-27-4 as follows. COA of Formula: C6H8N2O2
To an N,N-dimethylformamide solution (2.0 ml) of ethyl 1H-pyrazole-3-carboxylate (111 mg, 0.79 mmol), sodium hydride (60percent in oil, 70 mg, 1.75 mmol) was added under ice-cooling. The resulting mixture was stirred for 5 min. To the reaction mixture, an N,N-dimethylformamide solution (5.0 ml) of compound 26 (815 mg, 1.71 mmol) and tetrabutylammonium iodide (209 mg, 0.56 mmol) were added. While warming to room temperature, the resulting mixture was stirred for 14 h. The reaction mixture was concentrated in vacuo. To the residue, diethyl ether and distilled water were added. The organic layer was separated and dried over Na2SO4. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (methanol-dichloromethane = 1:100) to give the title compounds, 3-isomer (92 mg, 0.18 mmol, 10percent) and 5-isomer (78 mg, 0.15 mmol, 9percent), respectively. 3-isomer: MS (ESI) m/z 522 (M+H)+. 1H NMR (CDCl3) delta 1.38 (3H, t, J = 7.1 Hz), 2.56-2.69 (2H, m), 3.43 (3H, s), 3.86 (3H, s), 4.28-4.34 (1H, m), 4.38 (2H, q, J = 7.1 Hz), 4.43-4.63 (2H, m), 5.74 (1H, s), 6.27-6.32 (1H, m), 6.35-6.38 (1H, m), 6.71-6.77 (2H, m), 6.97 (1H, dd, J = 8.1, 1.5 Hz), 7.07-7.10 (1H, m), 7.21 (1H, t, J = 8.0 Hz), 7.29-7.39 (3H, m), 7.44 (1H, d, J = 2.2 Hz). 5-isomer: MS (ESI) m/z 522 (M+H)+. 1H NMR (CDCl3) delta 1.33 (3H, t, J = 7.1 Hz), 2.48-2.67 (2H, m), 3.43 (3H, s), 3.85 (3H, s), 4.30 (2H, q, J = 7.1 Hz), 4.38-4.46 (1H, m), 4.81-4.90 (2H, m), 5.72 (1H, s), 6.31-6.40 (2H, m), 6.73 (1H, d, J = 2.2 Hz), 6.81 (1H, d, J = 2.0 Hz), 6.95 (1H, dd, J = 8.1, 1.2 Hz), 7.08 (1H, t, J = 2.1 Hz), 7.19 (1H, t, J = 8.1 Hz), 7.28-7.38 (2H, m), 7.40-7.46 (2H, m).
According to the analysis of related databases, 5932-27-4, the application of this compound in the production field has become more and more popular.
Reference:
Article; Ichikawa, Masanori; Ohtsuka, Masami; Ohki, Hitoshi; Haginoya, Noriyasu; Itoh, Masao; Sugita, Kazuyuki; Usui, Hiroyuki; Suzuki, Makoto; Terayama, Koji; Kanda, Akira; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 3072 – 3093;,
Pyrazole – Wikipedia,
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