Ethyl 4-[2-fluoro-4-(2-[2-(3-hydroxy-4-methoxybenzylidene)hydrazino]-2-oxoethyl amino)phenyl]piperazine-1-carboxylate (19a) The mixture of solution of compound 9 (10 mmol) and 3-hydroxy-4-methoxybenzaldehyde (10 mmol) in absolute ethanol was irradiated c-Met inhibitor by microwave at 200 W and 140 °C for 30 min. MEK inhibitor Yield: 72 %. M.p: 183–185 °C. FT-IR (KBr, ν, cm−1): 3342, 3181 (2NH), 3096 (ar–CH), 1678 (2C=O), 1437 (C=N), 1211 (C–O). Elemental analysis for C23H28FN5O5 calculated (%): C, 58.34; H, 5.96; N, 14.79. Found (%): C, 58.65; H, 6.06; N, 14.98. 1H NMR (DMSO-d 6, δ ppm): 1.17 (t, 3H, CH3,

J = 6.8 Hz), 2.77 (s, 4H, 2CH2), 3.36 (s, 6H, 3CH2), 3.78 (s, 3H, O–CH3), 3.99 (q, 2H, CH2, J = 6.6 Hz), 5.80 (brs, 1H, NH), 6.04 (brs, 1H, NH), 6.32–6.37 (m, 3H, arH), 6.84–6.98 (m, 3H, arH), 9.27 (s, 1H, N=CH), 11.35 (s, 1H, OH). 13C NMR (DMSO-d 6, δ ppm): 15.26 (CH3), 44.29 (CH2), 44.62 (2CH2), 51.78 (2CH2), 56.22 (OCH3), 61.48 (CH2), arC: [101.23 (d, CH, J C–F = 22.0 Hz), 108.47 (CH), 112.58 (d, CH, J C–F = 15.0 Hz), 120.73 (CH), 120.96 (CH), 121.72 (CH), 127.64 (C), 129.83 (d, C, J C–F = 9.1 Hz), 146.25 (C), 146.46 (C), 150.34 (d, C, J C–F = 6.5 Hz), 151.36 (d, C, J C–F = 388.7 Hz)], 144.44 (N=CH), 167.17 (C=O), 171.66 (C=O). MS m/z (%): 497.56 ([M+1 + Na]+, 31) 496.56 ([M+Na]+,100), 370.41 (19), 360.65 (22). Ethyl 4-[2-fluoro-4-(2-oxo-2-[2-(pyridin-4-ylmethylene)hydrazino]selleck products ethylamino)phenyl] piperazine-1-carboxylate (19b) The mixture of compound 9 (10 mmol) and pyridine-4-carbaldehyde (10 mmol) Aprepitant in absolute ethanol was irradiated by microwave at 200 W and 140 °C for 30 min. On cooling the reaction mixture to room temperature a solid was appeared. This crude

product was recrystallized from ethanol. Yield: 85 %. M.p: 184–185 °C. FT-IR (KBr, ν, cm−1): 3356, 3269 (2NH), 3057 (ar–CH), 1707, 1679 (2C=O), 1428 (C=N), 1230 (C–O). Elemental analysis for C21H25FN6O3 calculated (%): C, 58.87; H, 5.88; N, 19.61. Found (%): C, 58.97; H, 6.00; N, 19.97. 1H NMR (DMSO-d 6, δ ppm): 1.16 (brs, 3H, CH3), 2.76 (s, 4H, 2CH2), 3.41 (s, 4H, 2CH2), 4.02–4.03 (m, 2H, CH2), 4.21 (s, 2H, CH2), 6.35–6.51 (m, 2H, arH), 6.83 (brs, 1H, arH), 7.69 (brs, 2H, arH), 8.63 (s, 3H, 2arH + CH), 11.80 (s, 2H, 2NH). 13C NMR (DMSO-d 6, δ ppm): 15.26 (CH3), 47.25 (CH2), 51.79 (2CH2), 52.85 (2CH2), 61.37 (CH2), arC: [107.70 (d, CH, J C–F = 45.1 Hz), 114.07 (C), 118.26 (d, CH, J C–F = 29.3 Hz), 120.15 (CH), 124.56 (2CH), 137.02 (C), 141.37 (d, C, J C–F = 50.6 Hz), 146.20 (2CH), 152.26 (d, C, J C–F = 161.2 Hz)], 150.31 (N=CH), 160.00 (C=O), 166.71 (C=O).