Potassium Sodium Tartrate → HCID 68999893, compound

Participants

Reaction Conditions

Reaction Steps

(E)-2-[2-(1H-indazol-3-yl)vinyl]-N-hydroxybenzamidine (0.08 g, 0.29 mmol) obtained in Step 1 of Example 175 was dissolved in pyridine (5.0 mL) and the solution was added with ethylsuccinyl chloride (47 μL, 0.33 mmol), followed by stirring at 90° C. for 1 hour. The reaction mixture was added with water and extracted with ethyl acetate. After the organic layer was concentrated, the residue was added to acetonitrile (5.0 mL) and stirred at 80° C. for 3.5 hours. The reaction mixture was added with water and extracted with ethyl acetate. After the organic layer was concentrated, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/2) and the residue was dried. Further, the residue was dissolved in a mixed solvent of methylene chloride (1.0 mL)/THF (1.0 mL), cooled to −78° C. and diisobutylaluminum hydride (1.0 mol/L toluene solution, 1.0 mL, 1.0 mmol) was added, followed by stirring for 30 minutes. The reaction mixture was added with saturated aqueous Rochelle salt solution, extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=2/1) to obtain Compound 180 (18 mg, 24%).

Provenance & Evidence