4'-Mercaptoacetanilide → HCID 178487269, compound

Participants

Reaction Conditions

Reaction Steps

3-Cyclopropyl-1H-pyrazol-5(4H)-one (0.2 mmol) and 4-chloro-6-methoxyquinoline 1-oxide (0.025 g, 0.2 mmol) were stirred in acetic anhydride (1.5 mL) at ambient temperature for 30-40 minutes. The reaction mixture was concentrated and the resulting solid filtered off and washed with a minimum amount of ether. (Z)-4-(4-chloro-6-methoxyquinolin-2(1H)-ylidene)-3-cyclopropyl-1H-pyrazol-5(4H)-one (0.04 g, 0.11 mmol) was dissolved in ethanol (1.5 mL) and 4-acetamidothiophenol (0.019 g, 0.11 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 the resulting solid filtered and washed with ether to give Example 47. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.46 (d, J=6.57 Hz, 2H) 0.65-0.71 (m, 2H) 1.43-1.54 (m, 1H) 2.11 (s, 3H) 3.98 (s, 3H) 7.18 (s, 1H) 7.45 (d, J=2.53 Hz, 1H) 7.63 (dd, J=9.09, 2.27 Hz, 1H) 7.70 (d, J=8.59 Hz, 2H) 7.82 (d, J=8.59 Hz, 2H) 8.07 (d, J=9.09 Hz, 1H) 10.39 (s, 1H); ESI-MS: m/z calc'd for C24H22N4O3S 446.52. found 447.2 (M+H)+.

Provenance & Evidence