6 Hz), 2.96 (s, 4H, 2CH2), 3.49 (s, 4H, 2CH2), 3.82 (s, 3H, O–CH3), 4.06 (q, 2H, CH2, J = 6.8 Hz), 6.71–6.78 (m, 1H, arH), 7.04–7.22 (m, 5H, arH), 7.86 (d, 1H, arH, J = 8.2 Hz), 8.58 (s, 1H, N=CH). 13C NMR (DMSO-d 6, δ ppm): 15.27 (CH3), 44.13 (CH2), 50.85 (CH2), 51.35 (2CH2), 56.10 (O–CH3) 61.53 (CH2), arC: [109.73 (d, CH, J C–F = 38.9 Hz), 114.98 (2CH), 118.72 (CH), 121.90 (d, CH, J C–F = 66.3 Hz), 129.12

(C), 131.24 (2CH), 132.53 (C), 138.35 (d, C, J C–F = 21.0 Hz), 147.24 (C), 154.40 (d, C, J C–F = 94.5 Hz), 160.10 (N=CH), 162.24 (C=O). Ethyl 4-(2-fluoro-4-[1H-indol-3-ylmethylene]aminophenyl)piperazine-1-carboxylate (4f) The solution of compound 3 (10 mmol) in absolute ethanol was refluxed with indol-3-carbaldehyde (10 mmol) for 6 h. On cooling the reaction content to room GDC-0449 supplier temperature, BMN-673 a solid appeared. This crude product was filtered off and recrystallized from acetone. Yield: 82 %. M.p: 184–186 °C. FT-IR (KBr, ν, cm−1): 3484 (NH), 1678 (C=O),

1439 (C=N), 1220 (C–O). Elemental analysis for C22H23FN4O2 calculated (%): C, 66.99; H, 5.88; N, 14.20. Found (%): C, 66.76; H, 6.02; N, 14.01. 1H NMR (DMSO-d 6, δ ppm): 1.20 (brs, 3H, CH3), 3.01 (s, 4H, 2CH2), 3.53 (s, 4H, 2CH2), 4.06 (brs, 2H, CH2), 7.29 (brs, 5H, arH), 8.08 (s, 1H, arH), 8.38 (s, 2H, arH), 9.06 (s, 1H, N=CH), 9.29 (s, 1H, NH). 13C NMR (DMSO-d 6, δ ppm): 15.21 (CH3), 44.18 (CH2), 50.76 (CH2), 51.51 (2CH2), 62.46 (CH2), arC: [108.93 (d, CH, J C–F = 23.4 Hz), 113.47 (d, CH, J C–F = 34.4 Hz), 117.88 (CH), 118.82 (C), 120.71 (CH), 121.51 (CH), 121.84 (CH), 122.84 (CH), 123.76 (d, CH, J C–F = 41.0 Hz), 124.87 (C), 137.91 (d, C, J = 19.8 Hz), 139.24 selleck dipyridamole (2C) 155.26 (d, C, J C–F = 4.0 Hz)], 153.18 (N=CH), 185.74 (C=O). Ethyl 4-(4-[(benzylamino)carbonyl]amino-2-fluorophenyl)piperazine-1-carboxylate (5) The mixture of compound 3 (10 mmol) and benzylisothiocyanate (10 mmol) in absolute ethanol was refluxed for 10 h. On cooling the reaction mixture to room temperature, a solid formed. This crude product was collected by filtration and recrystallized from ethanol.

Yield: 93 %. M.p: 153–155 °C. FT-IR (KBr, ν, cm−1): 3346, 3284 (2NH), 3063 (ar–CH), 1694, 1638 (2C=O), 1236 (C–O). Elemental analysis for C21H25FN4O3 calculated (%): C, 62.99, H, 6.29; N, 13.99. Found (%): C, 62.78; H, 6.07; N, 14.04. 1H NMR (DMSO-d 6, δ ppm): 1.17 (t, 3H, CH3, J = 7.6 Hz), 2.85 (s, 4H, 2CH2), 3.40 (s, 4H, 2CH2 + H2O), 4.02 (q, 2H, CH2, J = 7.0 Hz), 4.26 (d, 2H, CH2, J = 6.0 Hz), 6.61 (brs, 1H, NH), 6.95 (s, 2H, arH), 7.21–7.31 (m, 6H, arH), 8.62 (s, 1H, NH).