1,2-Dichloroethane → 5-Phenyl-oxazole-4-carboxylic acid (1-{2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-1H-pyrazol-3-yl)-amide

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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 5-phenyl-oxazole-4-carboxylic acid (114 mg, 0.60 mmol) in CH2Cl2 (3.0 mL) was treated at rt with HOBt (98 mg, 0.72 mmol), EDC (289 mg, 1.51 mmol) DMAP (18 mg, 0.15 mmol) and the resulting mixture was stirred at rt for 30 min. 1-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-1H-pyrazol-3-ylamine (297 mg, 0.60 mmol) in CH2Cl2 (3.0 mL) was then added and the resulting mixture was stirred at rt for 16 h. CH2Cl2 (20 mL) followed by water (15 mL) were added and the aqueous phase was extracted with CH2Cl2. The combined organic phases were washed with water, brine, dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=1.17 min, [M+H]+=494.56.

Provenance & Evidence