Nitrogen → 5-Phenyl-oxazole-4-carboxylic acid [2-(5-acetyl-furan-2-ylmethyl)-thiazol-4-yl]-amide

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-phenyl-1,3-oxazole-4-carboxylic acid (41 mg, 0.21 mmol) in CH2Cl2 (2.0 mL) was treated sequentially with DMAP (6 mg, 0.05 mmol), HOBt (30 mg, 0.22 mmol), EDC.HCl (89 mg, 0.46 mmol) and DIPEA (0.13 mL, 0.74 mmol) and the resulting mixture was stirred at rt for 15 min. This solution was then added to a solution of 1-[5-(4-amino-thiazol-2-ylmethyl)-furan-2-yl]-ethanone hydrochloride (41 mg, 0.19 mmol) in dry CH2Cl2 (0.5 mL) and the reaction mixture was stirred for 16 h at rt. CH2Cl2 (20 mL) was then added and the org. phase was washed with water (15 mL) and brine (15 mL). The org. phase was then dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept:EA) gave the title compound as a brown foam. TLC: rf (1:1 hept-EA)=0.30. LC-MS-conditions 02: tR=1.04 min, [M+H]+=394.37.

Provenance & Evidence