[NH2:1][C:2]1[S:3][C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C1C=CN=CC=1.ClCCl>[C:24]([NH:1][C:2]1[S:3][C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1To a stirred cold mixture of ethyl 2-amino-4-phenylthiazole-5-carboxylate (1.24 g, 5.00 mmol), 4-dimethylaminopyridine (0.10 g, 16 mol %) and pyridine (4.0 mL, 10 equiv) in dichloromethane (20.0 mL) was added benzoyl chloride (0.70 g, 5.00 mmol) in dichloromethane (3 mL). The mixture was stirred at ambient temperature for 2 h, then washed with 5% hydrochloric acid solution, water, and dried over anhydrous sodium sulfate. Removal of the solvent afforded the title compound in 92% yield (1.62 g); 1H NMR (CDCl3, 300 MHz) δ 10.10 (s, 1H), 8.15 (d, J=7.2 Hz, 2H), 7.85-7.45 (m, 8H), 4.24 (q, J=5.9 Hz, 2H), 1.19 (t, J=5.9 Hz, 3H); MS (ES+) m/z 353.1 (M+1).
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