[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:2]=1.[NH2:15][C:16]1[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=1.C(O)(=O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH:15][C:16]3[S:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=3)=[CH:9][CH:8]=2)[CH:2]=1To a 250 mL round-bottomed flask was added 4-(pyridin-3-yl)benzaldehyde (4 g, 21.8 mmol), methyl 2-aminothiazole-5-carboxylate (3.45 g, 21.83 mmol) and acetic acid (0.375 ml, 6.55 mmol) in toluene (109 ml). The reaction mixture was heated at reflux under Dean-Stark conditions for 3 hours, cooled to room temperature, and the volatiles were removed by rotary evaporation. Methanol was added, the solution was cooled to 0° C., and sodium borohydride (1.322 g, 34.9 mmol) was carefully added. The reaction was stirred at 0° C. for 15 minutes and allowed to warm to room temperature while stirring for an additional 2 hour. The solids were filtered off, washed with water and dried under high vacuum to give the title compound which was used in the next step without further purification.
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