Reference of 63069-50-1, 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 63069-50-1 as follows.
Specifically, oxalyl chloride (0.72 mL, 8.36 mmol) was added over 10 min to a solution of linoleic acid (2 mL, 6.43 mmol) and DMF (3 drops) in DCM (10 mL) at 0 C, and the solution stirred at room temperature overnight. The solvent and excess oxalyl chloride was removed in vacuo and the residue redissolved in DCM (10 mL). This solution was added dropwise to a solution of 3-fluoro-4-aminobenzonitrile (0.79 g, 5.79 mmol) in DCM (10 mL) and Et3N (1 mL) that had been cooled in an ice bath. Upon complete addition, the solution was stirred at room temperature overnight. The solution was washed with saturated Na2C03 solution (3 chi 20 mL), H20 (20 mL), and brine (20 mL), and dried over MgS04. The resulting residue was subjected to column chromatography, using a gradient elution of EtOAc/petroleum spirits to afford the product as a pale yellow oil that solidified upon cooling. (0597) [00453] Yield: 0.98 g (39%). (0598) [00454] FT- 1 (ATR) Vmait crrr1 : 3328 br w, 2925 m, 2855 m, 2232 w, 1709 m, 1616 m, 1594 m, 1517 s. 1 H-NMR delta/ppm (d6-DMSO): 10.07 (1 H, s, NH) , 8.32 (1 H, m, Ar CH), 7.91 (1 H, dd, 3JH,F = 1 1 .1 Hz, 4JH,H = 1 .9 Hz, Ar CH), 7.68 (1 H, ddd, 3JH,H = 8.6 Hz, 4JH,H = 1 .9 Hz, 5JH,F = 0.9 Hz Ar CH), 5.28 – 5.43 (4 chi 1 H, 4 chi m, 4 chi olefinic CH), 2.77 (2H, m, CH2), 2.48 (2H, m, NHCOCH2), 2.00 – 2.10 (2 x 2H, 2 x m, 2 x CH2), 1 .61 (2H, m, CH2), 1 .24 – 1 .40 (7 chi 2H, 7 chi m, 7 chi CH2), 0.88 (3H, m, CH3). 13C-NMR delta/ppm (d6-DMSO): 172.4 (CONH), 151 .7 (d, 1 JC,F = 247 Hz, Ar CF), 131 .6 (d, 2JC,F = 1 1 .2 Hz, Ar C), 129.70 (olefinic CH), 129.68 (olefinic CH), 129.3 (d, 3JC,F = 3.5 Hz, Ar CH), 127.74 (olefinic CH), 127.71 (olefinic CH), 122.9 (d, 4JC,F = 2.9 Hz, Ar CH), 1 19.3 (d, 2JC,F = 23.4 Hz, Ar CH), 105.7 (d, 3JC,F = 9.3 Hz, Ar C), 1 17.9 (d, 3JC,F = 2.7 Hz, CN), 35.9 (NHCOCHs), 30.9 (CH2), 29.0 (CH2), 28.7 (CH2), 28.6 (CH2), 28.52 (CH2), 28.5 (CH2), 26.6 (CH2), (0599) 25.2 (CH2), 24.9 (CH2), 21 .9 (CH2), 13.9 (CH3).
According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.
Reference:
Patent; CURTIN UNIVERSITY; FALASCA, Marco; MASSI, Massimiliano; SIMPSON, Peter, Vernon; (181 pag.)WO2019/40992; (2019); A1;,
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