With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.16874-33-2,Tetrahydrofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.
To a 50 mL two-neck flask were added2-(7-fluoro-1-(2-fluorobenzyl)-1H-indazol-3-yl)pyrimidine-4,5,6-triamine (0.10 g, 0.27 mmol),tetrahydrofuran-2-carboxylic acid (0.035 g, 0.30 mmol) and N,N-dimethylformamide (10 mL).Then 0-(7 -azabenzotriazol-1-yl)-N,N,N’,N’-te-tramethyluronium hexafluorophosphate (0.12 g,0.32 mmol) and N,N-diisopropylethylamine (0.13 mL, 0.79 mmol) were added at 0 o C. Themixture was stirred for 6 hours under an ice-bath condition. The reaction mixture was pouredinto water (30 mL), and the resulting mixture was extracted with ethyl acetate (30 mL x 2). Thecombined organic layers were washed with water (50 mL) and saturated brine (50 mL), driedover anhydrous sodium sulfate and filtered. The filtrate was concentrated on a rotary evaporatorand the residue was purified by silica gel chromatograph (dichloromethane /methanol (v/v) =80/1, 0.5percent triethylamine) to give a white solid (0.081 g, 64.0percent). MS (ESI, pos. ion) m/z: 466.1 (M+1);1HNMR (400 MHz, DMSO-d6) 8 (ppm) 8.70 (s, 1H), 8.57 (d, J= 8.0 Hz, 1H), 7.35 (dd, J=14.0, 6.8 Hz, 1H), 7.29- 7.10 (m, 4H), 6.98 (t, J = 7.5 Hz, 1H), 6.00 (s, 4H), 5.84 (s, 2H), 4.46(dd, J = 7.9, 6.1 Hz, 1H), 3.99 (dd, J = 14.5, 7.0 Hz, 1H), 3.82 (dd, J = 13.7, 7.2 Hz, 1H), 2.22-2.03 (m, 2H), 1.98- 1.79 (m, 2H);19F NMR (376 MHz, DMSO-d6) 8 (ppm) -118.75 (d, J = 7.1 Hz), -134.30 (d, J = 7.2 Hz)., 16874-33-2
As the paragraph descriping shows that 16874-33-2 is playing an increasingly important role.
Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZUO, Yinglin; WANG, Xiaojun; YANG, Chuanwen; WANG, Jiancheng; CAO, Shengtian; WU, Fangyuan; ZHANG, Yingjun; GOLDMANN, Siegfried; (193 pag.)WO2018/188590; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem