Hydrazine → HCID 178507798, compound

Participants

Reaction Conditions

Reaction Steps

3-Cyclopropyl-3-oxo-propionic acid (0.5 g, 3.2 mmol) was stirred in ethanol and acetic acid (10:1, 2.2 mL) and treated with hydrazine (0.12 mL, 3.8 mmol). After 15 hrs, the solid was filtered off and washed with a minimum amount of ethanol. Then, the product (3-cyclopropyl-1H-pyrazol-5(4H)-one) (0.4 mmol) and 4-chloroquinoline N-oxide (0.087 g, 0.48 mmol) were stirred in acetic anhydride (1 mL) at ambient temperature for 20-30 minutes. The reaction mixture was concentrated and carried out to the next step with out any purification. The resulting (Z)-4-(4-chloroquinolin-2(1H)-ylidene)-3-cyclopropyl-1H-pyrazol-5(4H)-one was dissolved in ethanol (1.5 mL) and 4-acetamidothiophenol (0.076 g, 0.45 mmol) was added. The reaction mixture was heated to 180° C. using a microwave reactor for 30 minutes. The mixture was concentrated and purified by LC-MS to give the title compounds of Example 14 and Example 15.

Provenance & Evidence