Diisopropylethylamine → HCID 71667530, compound

Participants

Reaction Steps

5-Amino-2-ethoxy-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 8c (58.3 mg, 0.12 mmol, 100 mol %), 2-cyclopropyl-oxazole-4-carboxylic acid 1 h (27.9 mg, 0.18 mmol, 150 mol %) and N,N-diisopropylethylamine (0.06 ml, 0.36 mmol, 300 mol %) were combined in N,N-dimethylformamide (3.0 ml) and HATU (69.3 mg, 0.18 mmol, mol %) was added and the reaction was stirred at room temperature for 16 h. The reaction was then diluted with water and extracted three times with ethyl acetate. The combined organics were dried over sodium sulfate and then concentrated to a residue that was purified by reverse phase HPLC (methanol+0.1% formic acid/water) to afford 2-cyclopropyl-oxazole-4-carboxylic acid [4-ethoxy-5-[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide 8e (54.8 mg, 0.09 mmol, 73.3%) as a white solid.

Provenance & Evidence