75 (br s, lH), three.86 (s, 3H), 3.62 (m, 2H), 3.55 (s, 2H), 2.94 (t, 2H, J = six.82 Hz). Anal. (C13H15IN2O2) C, H, N. three.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 8, Figure six) N-Acylatedazaindole (compound 7, Figure 6) [19,20] (1.21 g, 3.four mmol) was solubilized inside a 1:10 water/methanol mixture. Potassium hydroxide (6.61 g, 118 mmol) was added as well as the reaction mixture refluxed for 87 h. Immediately after cooling, methanol was evaporated below reduced pressure and water (100 mL) added. The solution was extracted with ethyl acetate (3 ?50 mL) as well as the organic phases combined and washed having a saturated aqueous option of ammonium chloride (50 mL). The organic phase was dried more than magnesium sulfate, filtrated, and evaporated below reduced pressure. The crude product was purified by silica gel column chromatography (ethyl acetate 84/methanol 15/ammoniac 1) to get amine 8 as a colorless oil (0.62 g). Yield: 58 ; 1H NMR (CDCl3; 250 MHz): 8.Price of Dde-Dap(Fmoc)-OH 45 (br s, 1H), 7.92?.88 (m, 2H), 7.73 (d, J = eight.25 Hz, 1H), 7.58 (d, J = eight.75 Hz, 1H), 7.53?.39 (m, 4H), 6.64 (d, 1H), 4.00 (s, 3H), 3.37 (br s, 2H), 3.00 (t, J = 6 Hz, 2H), two.84 (t, J = 6 Hz, 2H); IR (neat, cm-1): 2,934, 1,613, 1,576, 1,242, 777; HRMS (ESI): calcd. for C20H20N3O [M+H]+ 318.160089; located 318.160154. three.9.2. Synthesis of 2-bromo-N-2-[5-methoxy-2-(naphthalen-1-yl)-1H-pyrrolo[3,2-b]pyridine-3-yl] Acetamide (Compound 9, Figure 6) A mixture of triethylamine (290 ; two.08 mmol) and amine eight (600 mg; 1.90 mmol) in dichloromethane (20 mL) was cooled at -10 . A remedy of bromoacetyl bromide (180 ; two.08 mmol) in dichloromethane (five mL) was added and the reaction mixture stirred for 1 h.Price of 1175052-07-9 Int.PMID:34816786 J. Mol. Sci. 2013,The resulting answer was washed with water (20 mL), and also the organic phase dried more than MgSO4 and evaporated under decreased stress. 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 strong. Yield: 59 ; 1H NMR (CDCl3; 250 MHz): eight.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), 6.69 (d, J = eight.75 Hz, 1H), 4.09 (s, 3H), 3.60 (s, 2H), three.57?.52 (m, 2H), two.93 (t, J = 6.25 Hz, 2H); Anal (C22H20BrN3O2)C, H, N; SM (ESI): m/z = 438 [M+H]+ (79Br), 440 [M+H]+ (81Br). Figure 6. Schematic representation from 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 six) A mixture of sodium iodide (115 mg; 0.77 mmol) and bromo derivative 9 (310 mg; 0.7 mmol) in dry acetone (five mL) was refluxed for 15 h. Immediately after cooling, the reaction was evaporated and dichloromethane (20 mL) added. The organic phase was washed with water (20 mL), dried more than MgSO4, filtered, and evaporated under lowered stress. The residue was purified by silica gel column chromatography (ethyl acetate 30/petroleum ether 70) to receive 160 mg in the preferred compound, S70254, following precipitation with ethyl acetate. Yield: 47 ; 1H NMR (CDCl3; 250 MHz): eight.23 (br, 1H), 7.96?.91 (m, 2H), 7.75?.67 (m, 2H), 7.64 (d, J = eight.75 Hz, 1H), 7.58?.43 (m, 4H), 6.70 (d, J = 8.75 Hz, 1H), four.10 (s, 3H), 3.50?.46 (m, 2H), three.45 (s, 2H), two.89 (t, J = six.five Hz, 2H); Anal (C22 H20 I N3 O2)C, H, N; SM (ESI): m/z = 486 [M+H]+. three.ten. Radio-Iodination three.ten.