As a common heterocyclic compound, it belongs to naphthyridine compound, name is 2-Methyl[1,8]-Naphthyridine, and cas is 1569-16-0, its synthesis route is as follows.,1569-16-0
A solution of 2-Methyl-l ,8-naphthyridine (0.037 g, 0.257 mmol), Intermediate 25 (0.100 g, 0.257 mmol) and 4-methylbenzenesulfonamide (0.044 g, 0.257 mmol) in toluene (0.555 mL) was stirred at 110 C for 14 h. After cooling to room temperature, the solvent was removed in vacuo and the residue was purified by preparative HPLC (Phenomenex Luna AXIA 5u21.2xl00 mm, 10 min gradient, 15 min run, 10% to 100% Solvent B = 90% MeOH-10% H2O-0.1%TFA, Solvent A = 10% MeOH-90% H2O-0.1%TFA) to afford TFA salts of IB and IE, respectively. These salts were individually dissolved in MeOH (1.000 mL) and 250 mg Dianion WA21J resin was added. After stirring at room temperarture for 1 h, the resin was removed by filtration and washed well with MeOH. The filtrates were concentrated in vacuo to afford IB (25.8 mg, 20%) as an orange-brown oil and IE (32.5 mg, 19%) as a brown oil, respectively. IB: NMR (500MHz, CDCb) 59.06 (dd,J=4.1, 1.9 Hz, 1H), 8.16-8.05 (m, 2H), (0395) 7.92 (d,J= 16.0 Hz, 1H), 7.54 (d,J= 8.3 Hz, 1H), 7.39 (dd,J= 8.0, 4.1 Hz, 1H), 7.25 (d, J= 1.4 Hz, 1H), 7.13-7.04 (m, 3H), 6.98 – 6.86 (m, 2H), 6.32 (dd,J=8.8, 7.2 Hz, 1H), 4.17 – 4.05 (m, 3H), 4.02 – 3.95 (m, 1H), 3.88 (s, 3H), 3.64 – 3.55 (m, 1H), 3.34 – 3.25 (m, 1H), 3.05 – 2.92 (m, 2H), 1.20 (t, J= 7.2 Hz, 3H). HPLC retention time (Method 1): 2.430 min.; LCMS (ES): m/z 515.1 [M+H]+ (0396) IE.: NMR (500MHz, CDCB) delta 9.04 (dd,J=4.1, 1.9 Hz, 1H), 8.07 (dt,J=8.0, 1.5 Hz, 2H), 7.95 (d, J= 8.3 Hz, 2H), 7.48 – 7.31 (m, 4H), 7.08 – 7.00 (m, 2H), 6.93 – 6.83 (m, 1H), 6.81 (d,J=1.7Hz, 1H), 6.52 (d,J=1.7Hz, 1H), 6.23 (dd,J=8.7, 7.3 Hz, 1H), 4.26 (t, J= 7.4 Hz, 1H), 4.07 (q, J= 7.1 Hz, 2H), 3.92 – 3.79 (m, 4H), 3.77 – 3.68 (m, 1H), 3.48 – 3.33 (m, 5H), 3.20 – 3.08 (m, 1H), 3.02 – 2.81 (m, 3H), 1.12 (t,J= 7.2 Hz, 3H). HPLC retention time (Method 1): 2.430 min.; LCMS (ES): m/z 659.2 [M+H]+.
With the complex challenges of chemical substances, we look forward to future research findings about 1569-16-0,belong naphthyridine compound
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; MIGNONE, James; (95 pag.)WO2019/94319; (2019); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem