Cl.[C:2]([OH:10])(=O)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[NH2:32][C:33]1[S:34][CH:35]=[C:36]([C:38]2[C:43]([CH3:44])=[CH:42][C:41]([OH:45])=[CH:40][C:39]=2[CH3:46])[N:37]=1>CN(C=O)C>[OH:45][C:41]1[CH:40]=[C:39]([CH3:46])[C:38]([C:36]2[N:37]=[C:33]([NH:32][C:2](=[O:10])[C:3]3[CH:4]=[CH:5][N:6]=[CH:7][CH:8]=3)[S:34][CH:35]=2)=[C:43]([CH3:44])[CH:42]=1
To a suspension of isonicotinic acid hydrochloride (1.48 g, 10.0 mmol, 1.2 equiv) in DMF was added EDC (3.90 g, 2.0 equiv), HOBt (2.7 g, 2.0 equiv) and NEt3 (3.03 g, 3.0 equiv). After being stirred at room temperature for 1.0 h, the solution was added with 4-(2-aminothiazol-4-yl)-3,5-dimethylphenol (5-2, 2.2 g, 1.0 equiv). The reaction mixture was stirred at room temperature overnight. The solution was concentrated and the residue was re-dissolved in EtOAc. The solution was washed with brine, dried over MgSO4, and concentrated under reduced pressure to give brown solid. The brown solid was washed with 50% EtOAc in hexanes to give 5-3 (2.08 g) as white solids in 64% yield: 1H NMR (500 MHz, CDCl3) δ 9.29 (s, 1 H), 8.80 (d, 2 H), 7.98 (d, 2 H), 7.06 (s, 1 H), 6.51 (s, 2 H), 2.01 (s, 6H).
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