Cl.[F:2][C:3]([F:12])([F:11])[C:4]1[CH:8]=[C:7]([CH2:9][NH2:10])[NH:6][N:5]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:25]([CH3:29])[C:26](O)=[O:27])[CH:17]=[CH:18][C:19]=1[CH2:20][S:21]([CH3:24])(=[O:23])=[O:22].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>C1COCC1>[F:13][C:14]1[CH:15]=[C:16]([CH:25]([CH3:29])[C:26]([NH:10][CH2:9][C:7]2[NH:6][N:5]=[C:4]([C:3]([F:2])([F:11])[F:12])[CH:8]=2)=[O:27])[CH:17]=[CH:18][C:19]=1[CH2:20][S:21]([CH3:24])(=[O:22])=[O:23]To a stirred solution of (3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (194 mg, 0.96 mmol) and 2-(3-fluoro-4-(methylsulfonylmethyl)phenyl)propanoic acid (250 mg, 0.96 mmol) in THF (7.4 mL) were added O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluorborat (308 mg, 0.96 mmol), 1-hydroxybenzotriazole (135 mg, 0.96 mmol) and N-ethyldiisopropylamine (0.491 mL, 2.881 mmol). The reaction mixture was stirred for overnight at room temperature, concentrated in vacuo, purified by CC (eluent: ethyl acetate/cyclohexane (9:1)) to give 2-(3-fluoro-4-(methylsulfonylmethyl)phenyl)-N-((3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide (335 mg, 86%).
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