[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7](F)[C:3]=1[C:4]([OH:6])=[O:5].Cl.CN.[CH2:16]([N:18](CC)CC)C>N1C=CC=CC=1>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([NH:18][CH3:16])[C:3]=1[C:4]([OH:6])=[O:5]To a solution of 2,4,6-trifluorobenzoic acid (6.0 g, 34.1 mmol) and methylamine hydrochloride (12.0 g, 170 mmol) in pyridine (24 mL), triethylamine (24 mL, 170 mmol) was added. The reaction was stirred at 110° C. for 15 h and then concentrated in vacuo. The residue was acidified with 1N HCl (100 mL). The precipitate was collected by filtration to give 5.83 g of clean desired product as an orange solid (91%). 1H NMR (400 MHz, DMS O-d6): δ 13.09 (s, 1H), 7.91 (s, 1H), 6.33 (s, 1H), 6.30 (s, 1H), 2.81 (s, 3H). MS (ES) [m+H] calc'd for C8H7F2NO2, 188; found 188.
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