[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4](O)=[O:5].CC[N:15]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.N>O1CCCC1>[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4]([NH2:15])=[O:5]To a solution of 2-amino-4-chloro-6-fluorobenzoic acid (3.22 g, 17.04 mmol) in tetrahydrofuran (100 mL) was added EDCI.HCl (6.5 g, 34.1 mmol, Aldrich), HOBT (4.6 g, 34 mmol) and ammonia as a 0.5M solution in dioxanes (170 mL, 85 mmol, Aldrich). The resultant slurry was stirred for 24 hours, and then solids removed by filtration through celite. The filtrate was taken to a residue under reduced pressure and partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by chromatography on SiO2 (Ethyl acetate/Hexanes) to afford analytically pure 2-amino-4-chloro-6-fluorobenzamide as a white crystalline solid (2.98 g, 92% Yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.40 (s, 2 H), 6.44 (dd, J=10.81, 2.02 Hz, 1 H), 6.57 (s, 1 H), 7.56 (s, 1 H), 7.60 (s, 1 H).
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