4-Aminopyridine → 2-{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-N-pyridin-4-yl-benzamide

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Reaction Steps

To 2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid (0.051 g, 0.150 mmol) in 2 mL of CH2Cl2 at 4° C. is added 2 M oxalyl chloride solution (0.100 mL, 0.200 mmol) and 2 drops of dry DMF. The mixture is allowed to warm to room temperature over 1 h. To this is added 4-aminopyridine in one portion and diisopropylethyl amine (0.100 mL, 0.310 mmol). The mixture is stirred for 16 h. The mixture is concentrated and then purified via preparative HPLC (20-80% CH3CN/H2O). The product is further purified using a SiO2 prep-plate, eluting with (10% MeOH/CH2Cl2) to give 0.032 g of the title compound in 63% yield. MS MH+=419.2

Provenance & Evidence