The AZD4547 solid click here obtained was recrystallized from ethanol. Elemental analysis for C13H18FN3O2 calculated (%): C, 58.41; H, 6.79; N, 15.72. Found (%): C, 58.31; H, 6.87; N, 15.78. 1H NMR (DMSO-d 6, δ ppm): 1.18 (t, 3H, CH3, J = 7.0 Hz), 2.76 (s, 4H, 2CH2), 3.45 (s, 4H, 2CH2), 4.04 (q, 2H, CH2, J = 7.4 Hz), 5.03 (s, 2H, NH2), 6.33 (d, 2H, arH, J = 12.4 Hz), 6.76 (t, 1H, arH, J = 9.0 Hz). 13C NMR (DMSO-d 6, δ ppm): 14.53 (CH3), 43.56 (2CH2), 51.07 (2CH2), 60.75 (CH2), arC: [101.66 (d, CH, J C–F = 23.0 Hz), 109.39 (CH), 120.92 (d, CH, J C–F = 4.05 Hz), 128.70 (d, C, J C–F = 9.5 Hz), 145.72 (d, C, J = 10.6 Hz), 154.18 (d, C, J C–F = 34.5 Hz)], 158.65 (C=O). MS m/z (%): 268.10 ([M+1]+,100). Ethyl 4-(2-fluoro-4-[pyridin-4-ylmethylene]aminophenyl)piperazine-1-carboxylate (4a) Indole-3-carboxaldehyde (10 mmol) was added to the solution of compound 3 (10 mmol) in absolute ethanol and the reaction mixture was irradiated by microwave at 150 W and 110 °C for 30 min. After removing in the solvent under reduced pressure, an oily product obtained. This was recrystallized from butyl acetate and diethyl ether (1:2). Yield:
81 %, M.p: 162–163 °C. FT-IR (KBr, ν, cm−1): 1686 (C=O), 1508 (C=N), 1224 (C–O). Elemental analysis for C19H21FN4O2 calculated (%): C, 64.03; H, 5.94; N, 15.72. Found (%): C, 64.18; H, 6.14; N, 15.78. CT99021 ic50 1H NMR (DMSO-d 6, δ ppm): 1.19 (t, 3H,
CH3, J = 6.6 Hz), 3.00 (s, 4H, 2CH2), 3.51 (s, 4H, 2CH2 + H2O), 4.04–4.11 (m, 2H, CH2), 7.04–7.34 (m, 3H, arH), 7.80 (d, 2H, arH, J = 4.2 Hz), 8.71 (s, 3H, arH + N=CH). 13C NMR (DMSO-d 6, δ ppm): 15.26 (CH3), selleck chemical 44.01 (CH2), 50.69 (CH2), 51.83 (2CH2), 61.57 (CH2), arC: [102.18 (CH), 109.63 (d, CH, J C–F = 21.0 Hz), 120.05 (d, CH, J C–F = 31.5 Hz), 121.37 (C), 122.77 (2CH), 139.48 (d, C, J C–F = 9.0 Hz), 144.37 (d, C, J C–F = 120.0 Hz), 151.14 (2CH), 154.23 (d, C, J C–F = 103.2 Hz)], 158.09 (N=CH), 158.90 (C=O). MS m/z (%): 357.11 ([M+1]+, 64), 302.10 (100), 342.24 (80). Ethyl 4-(2-fluoro-4-[(4-nitrophenyl)methylene]aminophenyl)piperazine-1-carboxylate (4b) The mixture of compound 3 (10 mmol) and 4-nitrobenzaldehyde (10 mmol) in absolute ethanol was irradiated by microwave at 150 W and 110 °C for 10 min. The solid obtained was recrystallized from ethyl acetate:petroleum ether (1:2). Yield: 58 %, M.p: 164–166 °C. FT-IR (KBr, ν, cm−1): 3074 (ar–CH), 1696 (C=O), 1510, and 1341 (NO2), 1433 (C=N), 1215 (C–O).