1-Methyl-3-n-propyl 2-pyrazolin-5-one (0.2 g, 1.4 mmol) and 4-chloroquinoline N-oxide (1.4 mmol) were stirred in acetic anhydride (2 mL) at ambient temperature for 2-3 hours. The reaction mixture was concentrated and carried out to the next step without further purification. The resulting (Z)-4-(4-chloroquinolin-2(1H)-ylidene)-1-methyl-3-propyl-1H-pyrazol-5(4H)-one (0.71 mmol) was dissolved in ethanol (0.5 mL) and 4-acetamidothiophenol (0.13 g, 0.78 mmol) was added. The reaction mixture was heated to 180° C. using a microwave reactor for 5-10 minutes. The mixture was then concentrated and purified by LC-MS to give Example 56. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.67 (t, J=7.45 Hz, 3H) 1.23-1.32 (m, J=7.52, 7.52, 7.52, 7.52 Hz, 2H) 2.00 (t, J=7.58 Hz, 2H) 2.09 (s, 3H) 3.29 (s, 3H) 6.53 (s, 1H) 7.52-7.57 (m, 1H) 7.67-7.76 (m, 3H) 7.80-7.90 (m, 3H) 8.06 (d, J=8.08 Hz, 1H) 10.34 (s, 1H); ESI-MS: m/z calc'd for C24H24N4O2S 432.54. found 433.3 (M+H)+.
