100491-29-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0,the naphthyridine compound, it is a common compound, a new synthetic route is introduced below.
General procedure: Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) / carboxylic acid (2) (0.001 mol) and appropriate substituted benzazol-2-thiol derivative (0.001 mol) or N,N- dimethyl-(3-piperazin-1-yl)propan-1-amine (0.001 mol) and K2CO3 were dissolved in acetone (30 mL). The solution was refluxed at 40 C for 12 h. Reaction mixture was cooled down and adjusted to pH=7 by AcOH. Acetone was evaporated, the residue was washed with water, filtered, dried and recrystallized from EtOH. Ethyl 7-((benzo[d]thiazol-2-yl)thio)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (3) Yield: 86 %, M.P. = 184.7 C. HPLC: 99.6 % purity. FTIR (ATR, cm-1 ): 1736 (C=O, ester), 1624 (C=O, ketone), 1043, 806, 750. 1H-NMR (300 MHz, DMSO-d6): delta = 1.25 (3H, t, J= 7.05 Hz , -CH3), 4.22 (2H, q, J= 7.05 Hz , -CH2-), 6.96-7.08 (2H, m, phenyl H(3), H(5)), 7.54-7.59 (2H, m, benzothiazole H(5), H(6)), 7.60-7.69 (1H, m, phenyl H(6)), 7.96-8.00 (1H, s, benzothiazole H(4), H(7)), 8.40 (1H, d, J= 8.85 Hz, naphthyridine H(5)), 8.64 (1H, s, naphthyridine H(2).13C-NMR (75 MHz, DMSO-d6): delta = 14.60, 60.81, 105.14 (q, J= 23.5 Hz), 112.49 (d, J= 22.6 Hz), 113.04, 121.01 (d, J= 19.1 Hz), 121.77 (d, J= 2.9 Hz), 122.04, 123.26, 124.28 (d, J= 13.3 Hz), 126.65, 127.14, 131.69 (d, J= 10.3 Hz), 137.28, 146.16, 149.15 (d, J= 21.0 Hz), 149.62, 152.03, 152.98 (d, J= 253.5 Hz), 155.09 (d, J= 3.4 Hz), 157.97 (dd, J= 250.7 Hz- 13.4 Hz), 162.77 (dd, J= 248.1 Hz- 11.6 Hz), 163.80, 173.15. HRMS (m/z): [M+H]+ calcd for C24H14N3O3S2F3: 514.0501; found 514.0492.
The chemical industry reduces the impact on the environment during synthesis,100491-29-0,Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,I believe this compound will play a more active role in future production and life.
Reference£º
Article; Gencer, Huelya Karaca; Levent, Serkan; Acar Cevik, Ulviye; Oezkay, Yusuf; Ilg?n, Sinem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1162 – 1168;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem