1,2-Dichloroethane → N-(2-((4-(methoxymethyl)thiazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-5-phenyloxazole-4-carboxamide

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Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 5-phenyloxazole-4-carboxylic acid (64 mg, 0.33 mmol) in CH2Cl2 (3.0 mL) was treated at rt with DMAP (10 mg, 0.08 mmol), HOBt (55 mg, 0.39 mmol), EDC (157 mg, 0.82 mmol) and DIPEA (0.25 mL, 1.48 mmol) and the resulting mixture was stirred for 15 min at rt. A solution of 2-((4-(methoxymethyl)thiazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine (74 mg, 0.33 mmol) in CH2Cl2 (3.5 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (15.0 mL), the layers were separated and the org. phase was washed with 1N HCl (15.0 mL), water (10.0 mL), followed by brine (10.0 mL) and dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (gradient from 90:10 hept-EA to 60:40 hept-EA) gave the title compound as a white solid. TLC: rf (7:3 hept-EA)=0.15. LC-MS-conditions 07: tR=0.83 min, [M+H]+=397.21

Provenance & Evidence