Extracurricular laboratory: Synthetic route of 178388-79-9

According to the analysis of related databases, 178388-79-9, the application of this compound in the production field has become more and more popular.

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 178388-79-9 as follows. Recommanded Product: 178388-79-9

A mixture of compound 5b (128 mg, 0.3 mmol), imidazole-4-propionic acid (1.26 g, 9 mmol; 30 eq.; prepared from urocanic acid by catalytic hydrogenation using 10% Pd-C in acetic acid, following the procedure described in J. Altman, N. Shoef, M. Wilchek, and A. Warshawsky J. Chem. Soc., Perkin Trans. I, 1984, 59), copper powder (38 mg, 0.6 mmol; 2 eq.), potassium carbonate (83 mg, 0.6 mmol; 2 eq.) was flushed with anhydrous nitrogen and heated in a sealed tube at 190-200 C. (oil bath temp.) for 2 h. Upon cooling, to the mixture was added MeOH, and the insoluble material was filtered. The filtrate was concentrated in vacuo and purified by C-18 reverse phase column (YMC, eluting with 15% CH3CN-water containing 0.1% TFA) to obtain 12 mg (0.023 mmol, Y. 7.5%) of the title compound Example 329 as amorphous powder (about 1:1 mixture of two regio-isomers): HPLC purity 96% (AP, at 254 nm); MS (LC/MS) m/z 531 (M+H); 1H NMR (CD3OD) delta ppm 2.74, 3.00 (2H, 2t, J=7 Hz), 2.82, 3.11 (2H, 2t, J=7 Hz), 3.59 (4H, br, CH2N), 3.79 (4H, br, CH2N), 3.79, 4.10 (3H, 2s, CH3O), 6.73 (s), 7.33 (s), 7.48 (5H, br. s, Ar-Hs), 7.93 (br.s), 8.00 (s), 8.10 (s), 8.40 (s), 8.77 (s), 9.43 (br.s).

According to the analysis of related databases, 178388-79-9, the application of this compound in the production field has become more and more popular.