0.012 mol), EDCI (1.86 g, 0.0012 mol), and HOBt (1.62 g, 0.0012 mol) had been added, and the mixture stirred at 0 for 30 min. A remedy of 5-methoxy tryptamine (1.9 g, 0.01 mol) in 10 mL of methylene chloride was cooled at 0 and added drop-wise. Just after six h of stirring at space temperature, the reaction mixture was washed with water, a 1M HCl solution, water, a ten NaOH remedy, and water until a pH of 7 was reached. The organic phase was dried over MgSO4, filtered, and concentrated below decreased stress. The residue was then crystallized from toluene, getting two.6 g (73 ) of SD6. Mp 159 ; 1H NMR (80 MHz, CDCl3) eight.32 (br s, 1H), 7.32 (d, 1H, J = 8.2 Hz ), six.96 (d, 1H, J = two.5Hz), 7.02 (d, 1H, J = two.three Hz), six.80 (dd, 1H, J = 2.5 Hz and eight.2 Hz), five.75 (br s, lH), 3.86 (s, 3H), three.62 (m, 2H), 3.55 (s, 2H), 2.94 (t, 2H, J = 6.82 Hz). Anal. (C13H15IN2O2) C, H, N. 3.9. Synthesis of S70254 three.9.1. Synthesis of 2-[5-methoxy-2-(naphthalen-1-yl)-1H-pyrrolo[3,2-b]pyridine-3-yl]ethan-1-amine (compound eight, Figure 6) N-Acylatedazaindole (compound 7, Figure six) [19,20] (1.21 g, three.four mmol) was solubilized within a 1:10 water/methanol mixture. Potassium hydroxide (6.61 g, 118 mmol) was added plus the reaction mixture refluxed for 87 h. Just after cooling, methanol was evaporated under lowered pressure and water (one hundred mL) added. The product was extracted with ethyl acetate (three 50 mL) and also the organic phases combined and washed using a saturated aqueous option of ammonium chloride (50 mL). The organic phase was dried over magnesium sulfate, filtrated, and evaporated below decreased pressure. The crude product was purified by silica gel column chromatography (ethyl acetate 84/methanol 15/ammoniac 1) to acquire amine eight as a colorless oil (0.62 g). Yield: 58 ; 1H NMR (CDCl3; 250 MHz): 8.45 (br s, 1H), 7.92.88 (m, 2H), 7.73 (d, J = 8.25 Hz, 1H), 7.58 (d, J = 8.75 Hz, 1H), 7.53.39 (m, 4H), 6.64 (d, 1H), 4.00 (s, 3H), three.37 (br s, 2H), three.00 (t, J = six Hz, 2H), 2.84 (t, J = six Hz, 2H); IR (neat, cm-1): 2,934, 1,613, 1,576, 1,242, 777; HRMS (ESI): calcd. for C20H20N3O [M+H]+ 318.160089; discovered 318.160154. 3.9.two. Synthesis of 2-bromo-N-2-[5-methoxy-2-(naphthalen-1-yl)-1H-pyrrolo[3,2-b]pyridine-3-yl] Acetamide (Compound 9, Figure six) A mixture of triethylamine (290 ; two.08 mmol) and amine 8 (600 mg; 1.90 mmol) in dichloromethane (20 mL) was cooled at -10 . A option of bromoacetyl bromide (180 ; 2.08 mmol) in dichloromethane (five mL) was added along with the reaction mixture stirred for 1 h.Int. J. Mol. Sci. 2013,The resulting answer was washed with water (20 mL), along with the organic phase dried over MgSO4 and evaporated beneath lowered stress.(±)-Clopidogrel (bisulfate) The residue was purified by silica gel column chromatography (ethyl acetate 30/petroleum ether 70) to get 320 mg of compound 9 (S70253) as a white solid.Lurbinectedin Yield: 59 ; 1H NMR (CDCl3; 250 MHz): eight.PMID:23558135 18 (br s, 1H), 7.97.92 (m, 2H), 7.74 (d, J = eight.25 Hz, 1H), 7.63 (d, J = 8.75 Hz, 1H), 7.56.43 (m, 5H), six.69 (d, J = eight.75 Hz, 1H), four.09 (s, 3H), 3.60 (s, 2H), 3.57.52 (m, 2H), two.93 (t, J = six.25 Hz, 2H); Anal (C22H20BrN3O2)C, H, N; SM (ESI): m/z = 438 [M+H]+ (79Br), 440 [M+H]+ (81Br). Figure six. Schematic representation of the synthesis of S72054.O HN O N N H eight O HN O N N H 9 S70254 Br NaI, acetone O N N H HN O I KOH, H2O/EtOH 7 O N BrCOCH2Br N H Et3N, CH2Cl2 NH3.9.three. Synthesis of 2-iodo-N-2-[5-methoxy-2-(naphthalen-1-yl)-1H-pyrrolo[3,2-b]pyridine-3-yl] Acetamide (S70254, Figure 6) A mixture of sodium iodide (115 mg; 0.77 mmol) and bromo derivative 9 (310 mg; 0.7 mm.