Cl.[NH2:2][C:3]1[N:8]=[C:7]([C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][C:4]=1[C:19]([OH:21])=[O:20].O[N:23]1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=[O:29].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[O:29]=[C:24]1[CH2:25][CH2:26][C:27](=[O:28])[N:23]1[O:20][C:19]([C:4]1[CH:5]=[CH:6][C:7]([C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:8][C:3]=1[NH2:2])=[O:21]6-Amino-3′-trifluoromethyl-[2,2′]bipyridinyl-5-carboxylic acid hydrochloride (11.33 g, 35.44 mmol), N-hydroxy-succinimide (8.15 g, 70.9 mmol), and EDCl (10.19 g, 53.16 mmol) are dissolved in a solution of dry THF (100 mL) and Hunig's base (16.12 g, 125 mmol). The reaction mixture is stirred overnight at room temperature. Ethyl acetate (200 mL) is added and the organic phase extracted with water (3×100 mL) and brine (100 mL). The organic extract is dried over Na2SO4 and the solvent removed under reduced pressure to yield the title compound as a brown foam.
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