Pyrazole → HCID 178456573, compound

Participants

Reaction Conditions

Reaction Steps

Compound 17 (100 mg, 0.21 mmol) obtained in Example 17 was dissolved in N,N-dimethylformamide (1 mL), to the solution were added pyrazole (28 mg, 0.42 mmol, 2.0 equivalents), and cesium carbonate (137 mg, 0.42 mmol, 2.0 equivalents) and the mixture was stirred at 120° C. for 2 hours. The reaction mixture was partitioned with ethyl acetate and water, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. After the organic layer was concentrated, diethyl ether and hexane were added to the concentrate and the resulting white solid (66 mg) was collected by filtration. The resulting product was dissolved in methanol (1 mL), to the solution were added ammonium formate (132 mg, 2.10 mmol) and 20% palladium hydroxide/carbon (30 mg), and then the mixture was stirred under reflux with heating for 3 hours. The reaction mixture was filtered by using Celite and concentrated, then to the concentrate were added ammonium formate (150 mg) and 20% palladium hydroxide/carbon (50 mg), and the mixture was stirred under reflux with heating for 4 hours. The reaction mixture was filtered by using Celite and concentrated, and the residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the title compound (40 mg, 52%) as a white solid.

Provenance & Evidence