Oxalyl chloride → HCID 59548757, compound

Participants

Reaction Steps

To a solution of 4-methanesulfonyl-benzoic acid (0.030 g, (0.150 mmol) in methylene chloride (2 mL) is added oxalyl chloride (0.017 mL, 0.200 mmol) followed by 1 drop of N,N-dimethylformamide. Vigourous bubbling is observed and the reaction mixture is stirred at room temperature for 2 h. The mixture is concentrated under a stream of nitrogen. The residue is dissolved in methylene chloride (2 mL) and 1-[4-(3-amino-5-chloro-pyridin-2-yl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone (0.040 g, 0.110 mmol) is added followed by (0.040 mL, 0.220 mmol) N,N-diisopropylethylamine (0.040 mL, 0.220 mmol). The mixture is stirred at room temperature for 3 days then concentrated under a stream of nitrogen. The residue is dissolved in dimethylsulfoxide and purified by reverse phase preparative HPLC to provide, after removal of the eluent, 0.022 g of N-(5-Chloro-2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-pyridin-3-yl)-4-methanesulfonyl-benzamide as a white solid in 36% yield. MS; MH+=531.8

Provenance & Evidence