[F:1][C:2]([F:13])([F:12])[C:3]1[C:8](C(O)=O)=[CH:7][N:6]=[CH:5][CH:4]=1.Cl.[CH3:15][O:16][C:17](=[O:39])[C@H:18]([CH2:35][CH2:36][S:37][CH3:38])[NH:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.ON1[C:46](=[O:47])C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C1C[O:66]CC1>C(OCC)(=O)C>[CH3:15][O:16][C:17](=[O:39])[C@H:18]([CH2:35][CH2:36][S:37][CH3:38])[NH:19][C:20](=[O:34])[C:21]1[CH:26]=[CH:25][C:24]([N:27]([C:8]2[CH:7]=[N:6][CH:5]=[CH:4][C:3]=2[C:2]([F:1])([F:12])[F:13])[C:46]([OH:47])=[O:66])=[CH:23][C:22]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1A mixture of 4-trifluoromethylnicotinic acid (100 mg, 0.523 mmol), (4-amino-2-phenylbenzoyl)methionine methyl ester hydrochloride (206 mg, 0.52 mmol), prepared as in Example 192B, 3-hydroxy1,2,3-benzotriazin-4(3H)-one (120 mg, 0.628 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (125 mg, 0.628 mmol) in THF (5 mL) was stirred 15 hours. The reaction mixture was diluted with ethyl acetate , washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (50% ethyl acetate-hexane) to give the title compound (157 mg, 57%).
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