[F:1][C:2]([F:9])([F:8])/[CH:3]=[CH:4]/[C:5](O)=[O:6].C(Cl)(=O)C(Cl)=O.[CH3:16][C:17]1[CH:22]=[C:21]([NH:23][CH:24]([CH3:27])[CH2:25][NH2:26])[CH:20]=[C:19]([CH3:28])[N:18]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O>[CH3:16][C:17]1[CH:22]=[C:21]([NH:23][CH:24]([CH3:27])[CH2:25][NH:26][C:5](=[O:6])/[CH:4]=[CH:3]/[C:2]([F:9])([F:8])[F:1])[CH:20]=[C:19]([CH3:28])[N:18]=1(E)-4,4,4-Trifluorobut-2-enoic acid (15.4 mg, 0.11 mmol) was dissolved in DCM (0.75 ml containing one drop of dimethyl formamide), oxalyl chloride was added (14 mg, 0.11 mmol) and the solution was stirred at room temperature for 15 minutes. This solution was added to a solution of N2-(2,6-dimethyl-4-pyridyl)propane-1,2-diamine (21.6 mg, 0.1 mmol) and diisopropylethylamine (44 μl, 0.25 mmol) dissolved in dimethylformamide (1 ml) and the resulting mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 10.7 mg (0.035 mmol, 35%).
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