[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C.[Cl:22][C:23]1[C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C(O)C(N)(CO)CO>C(Cl)Cl>[Cl:22][C:23]1[C:28]([C:29]([NH:12][C:9]2[CH:10]=[CH:11][C:6]([C:2]3[NH:1][CH:5]=[CH:4][N:3]=3)=[CH:7][CH:8]=2)=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1A slurry of 4-imidazolylphenylamine (15.9 mg, 0.100 mmol), polymer-supported DIPEA (0.100 g, 0.362 mmol, 3.62 mmol/g loading) in CH2Cl2 (2 ml) was treated with a 2-chloropyridine-3-carbonyl chloride solution (0.10 M, 0.200 mmol, 2.0 ml, 2.0 eq) in CH2Cl2. The mixture was vortexed at RT for 14 h. Afterwards, the excess acid chloride was removed by treating the reaction mixture with polymer-supported trisamine resin (0.100 g, 0.375 mmol, 3.75 mmol/g loading). The slurry was shaken at RT for an additional 18 h. The reaction mixture was filtered, rinsed with CH2Cl2 (1 ml), and the filtrate was concentrated under reduced pressure. The resulting brown oil was used directly in the subsequent reaction.
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