Diisopropylethylamine → HCID 56932828, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1,1-trifluoro-2-(4-((2S)-2-(((1-methylethyl)amino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.100 g, 0.203 mmol, Example 195, Step 1) in pyridine (3.0 mL) was added 4-dimethylaminopyridine (5.0 mg, 0.040 mmol), Hünig's base (0.1 mL, 0.6 mmol), and dimethylsulfamoyl chloride (0.05 mL, 0.4 mmol, Aldrich, St. Louis, Mo.). The resulting mixture was heated at 80° C. for 6 h. The reaction mixture was allowed to cool to room temperature and then partitioned between EtOAc (30 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (2×20 mL) and the combined organic extracts were dried over MgSO4, filtered, and concentrated. The crude product was purified by column chromatography (24 g of silica, 10% to 40% EtOAc in hexanes) to afford N,N-dimethyl-N′-(1-methylethyl)-N′-(((2R)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)sulfamide (0.010 g) as a mixture of two isomers:

Provenance & Evidence