Diisopropylethylamine → (R)-4'-Methyl-N-(1-(2-methylpyrimidin-5-yl)ethyl)-5-(methylsulfonyl)biphenyl-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4′-methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid (1.0 g, 3.44 mmol) in N,N-dimethylformamide (10 mL) were added (R)-1-(2-methylpyrimidin-5-yl)ethanamine (900 mg, 5.58 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (3.0 g, 7.89 mmol) and N,N-diisopropylethylamine (3.0 mL, 17.22 mmol). The reaction mixture was stirred for 16 hours at 25° C. LC-MS indicated the reaction was complete. The reaction solution was diluted with EtOAc and washed with water, sat. aq. NaHCO3, brine and dried over anhydrous MgSO4. The residue was purified by silica gel column and preparative HPLC to afford the final product as a light color solid.

Provenance & Evidence