Dimethylformamide → (S)-N2-((3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)-methyl)-N5-methylpyridine-2,5-dicarboxamide 2,2,2-trifluoroacetate

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To a 50 mL round bottom flask containing (S)-6-(((3-fluoropyridin-2-yl)-(4-(trifluoromethyl)phenyl)methyl)carbamoyl)nicotinic acid (Example 280) (86 mg, 0.205 mmol) was added DMF (3 mL). The resulting mixture was stirred at 23° C. for 2 min. At this time, DIPEA (143 μL, 0.820 mmol), methylamine (2.0 M in THF, 103 μL, 0.205 mmol) and then HATU (78 mg, 0.205 mmol) were added to the flask. The reaction was stirred for 1 h and then directly purified by reverse phase HPLC. The pure fractions were concentrated to give the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 9.85 (d, J=7.2 Hz, 1H), 9.00 (s, 1H), 8.55 (d, J=4.4 Hz, 1H), 8.20 (s, 2H), 7.60 (s, 4H), 7.52 (t, J=8.7 Hz, 1H), 7.45-7.34 (m, 1H), 6.74 (d, J=7.3 Hz, 1H), 6.55 (br. s., 1H), 3.07 (d, J=4.5 Hz, 3H). MS (ESI pos. ion) m/z: 433.1 (M+H).

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