N,N'-Dimethylethylenediamine → HCID 56932994, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-N-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-1-propanesulfonamide (0.130 g, 0.228 mmol) in DMF (3.0 mL) was added 3-iodopyridine (0.094 g, 0.46 mmol, Sigma-Aldrich, St. Louis, Mo.), N,N′-dimethylethylenediamine (0.020 mL, 0.18 mmol, Sigma-Aldrich, St. Louis, Mo.), copper(i) iodide (0.022 g, 0.11 mmol, Sigma-Aldrich, St. Louis, Mo.), cesium carbonate (0.223 g, 0.685 mmol, Sigma-Aldrich, St. Louis, Mo.), and water (0.300 mL). The resulting mixture was heated at 120° C. under N2 for 5 days. The reaction mixture was filtered through the Celite® (diatomaceous earth) and the filtrate was concentrated. The residue was purified by column chromatography (24 g of silica, 1% to 5% (2M NH3 in MeOH) in DCM) to afford 2-methyl-N-3-pyridinyl-N-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-1-propanesulfonamide (15 mg) as a mixture of 2 isomers.

Provenance & Evidence