N,N'-Dimethylethylenediamine → HCID 56932994, compound

Participants

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, Example 210) in DMF (3.0 mL) was added 3-iodopyridine (0.094 g, 0.46 mmol, Aldrich, St. Louis, Mo.), N,N′-dimethylethylenediamine (0.020 mL, 0.18 mmol, Aldrich, St. Louis, Mo.), CuI (0.015 mg, 0.21 mmol, Aldrich, St. Louis, Mo.), cesium carbonate (0.22 g, 0.69 mmol), and water (0.30 mL). The resulting mixture was heated at 120° C. for 14 d, with additional aliquots of 3-iodopyridine (50 mg, 0.23 mmol) being added on 2nd and 5th day. The reaction mixture was then filtered and the filtrate was concentrated. The crude product was purified by column chromatography (24 g of silica gel, 1 to 5% 2M NH3 in MeOH in CH2Cl2) 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 (0.015 mg) as a mixture of two isomers.

Provenance & Evidence