Diisopropylethylamine → 6-(methylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[4-(trifluoromethyl)phenyl]-N-[(1R)-2,2,2-trifluoro-1-phenylethyl]-4-quinolinecarboxamide

Participants

Reaction Conditions

Reaction Steps

6-(Methylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[4-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (100 mg, 0.162 mmol), dichloromethane (1621 μL), DIEA (31.2 μL, 0.178 mmol), and [(1R)-2,2,2-trifluoro-1-phenylethyl]amine (37.7 mg, 0.178 mmol) were combined in a round bottom flask. The mixture was cooled to 0° C. and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane 2,4,6-trioxide (145 μL, 0.243 mmol) (50% in EtOAc) was added dropwise. The mixture was stirred at 0° C. for 2 h, warmed to room temperature, and stirred overnight. The next day 0.1 mL of water and 2 mL of CH3CN were added, and the solution was concentrated to afford a yellow residue. The residue was dissolved in MeOH/DMSO and purified by reverse phase HPLC to afford the title compound as a white solid (32 mg, 27%). MS (m/z) 735.3 (M+H+).

Provenance & Evidence