CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:22]1([CH3:40])[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=[C:30]([C:36]([F:39])([F:38])[F:37])[N:29]=2)[CH:23]=1.[C:41]([C:43]1[CH:48]=[CH:47][C:46]([CH:49]([CH3:53])[C:50](O)=[O:51])=[CH:45][C:44]=1[F:54])#[N:42].C(N(CC)CC)C>>[C:41]([C:43]1[CH:48]=[CH:47][C:46]([CH:49]([CH3:53])[C:50]([NH:35][CH2:34][C:33]2[C:28]([C:24]3[CH:23]=[C:22]([CH3:40])[CH:27]=[CH:26][CH:25]=3)=[N:29][C:30]([C:36]([F:37])([F:39])[F:38])=[CH:31][CH:32]=2)=[O:51])=[CH:45][C:44]=1[F:54])#[N:42]N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (1.5 equiv), 1-hydroxybenzotriazole (1.5 equiv), and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (1 equiv) are added to a solution of 2-(4-cyano-3-fluorophenyl)propanoic acid (5 equiv) drop-wise triethylamine (2.5 equiv). The reaction mixture is stirred overnight at room temperature. The reaction is quenched with water and extracted with ethyl acetate. The extracted organic layer is dried over magnesium sulfate. After evaporate solvent, purified by column chromatographic purification (ethylacetate:hexane) afforded 2-(4-cyano-3-fluorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide.
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