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

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A suspension of 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.125 g, 0.223 mmol), [(1R)-2,2,2-trifluoro-1-phenylethyl]amine (0.061 g, 0.289 mmol), N,N-diisopropylethylamine (0.117 mL, 0.668 mmol), and T3P (propylphosphonic anhydride, 0.170 mL of a 50% w/v solution in ethyl acetate, 0.289 mmol) in dichloromethane (3.42 mL) was stirred at room temperature for 20 h. Additional portions of [(1R)-2,2,2-trifluoro-1-phenylethyl]amine (0.031 g, 0.145 mmol) and T3P (propylphosphonic anhydride, 0.085 mL of a 50% w/v solution in ethyl acetate, 0.145 mmol) were added, and the mixture stirred for 2 h. Water (2 mL) was added, and the mixture was poured through a hydrophobic frit. The isolated organic phase was absorbed onto florisil and purified via column chromatography (ISCO, 4 g silica, 1-6% methanol/methylene chloride) to afford 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-N-[(1R)-2,2,2-trifluoro-1-phenylethyl]-4-quinolinecarboxamide (0.048 g, 28% yield). MS (m/z) 719.2 (M+H+).

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