CCN(C(C)C)C(C)C.[CH3:10][N:11]1[CH:15]=[C:14]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)[CH:13]=[N:12]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:53][CH2:54][C:55]([N:57]1[CH2:62][CH2:61][N:60]([C:63](=[O:74])[C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=2[C:70]([F:73])([F:72])[F:71])[CH2:59][CH2:58]1)=[O:56]>CN(C=O)C.O>[CH3:10][N:11]1[CH:15]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([NH:53][CH2:54][C:55](=[O:56])[N:57]3[CH2:58][CH2:59][N:60]([C:63](=[O:74])[C:64]4[CH:69]=[CH:68][CH:67]=[CH:66][C:65]=4[C:70]([F:71])([F:73])[F:72])[CH2:61][CH2:62]3)=[O:22])=[CH:23][CH:24]=2)[CH:13]=[N:12]1DIPEA (76.2 mg, 0.09 mL, 0.59 mmol) was added to a stirred solution of 4-(1-methyl-1H-pyrazol-4-yl)-benzoic acid (40 mg, 0.19 mmol) in DMF (1 mL). HOBT (32 mg, 0.23 mmol) and EDCI (46 mg, 0.23 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone trifluoroacetic acid salt (102 mg, 0.23 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 50 mg (50.5% yield) of 4-(1-methyl-1H-pyrazol-4-yl)-N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-benzamide. LCMS Purity: 90.78%. 1H NMR (DMSO-d6): δ 8.6-8.5 (bt, 1H), 8.3-8.2 (s, 1H), 8.0-7.8 (s, 1H), 7.9-7.84 (m, 3H), 7.8-7.74 (m, 1H), 7.74-7.6 (m, 3H), 7.6-7.5 (m, 1H), 4.2-4.1 (m, 2H), 3.9-3.88 (s, 3H), 3.84-3.68 (m, 2H), 3.68-3.54 (m, 2H), 3.54-3.4 (m, 2H), 3.22-3.0 (m, 2H).
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