Diisopropylethylamine → HCID 89692816, compound

Participants

Reaction Steps

5-Amino-2-cyclopropyl-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-4-(4-o-tolyl-piperazin-1-yl)-benzamide 5b (89.0 mg, 0.19 mmol, 100 mol %), 2-cyclopropyl-oxazole-4-carboxylic acid 1h (43.0 mg, 0.28 mmol, 150 mol %) and N,N-diisopropylethylamine (0.10 ml, 0.56 mmol, 300 mol %) were combined in N,N-dimethylformamide (3.0 ml) and HATU (106.7 mg, 0.28 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 column chromatography (dichloromethane to 10% methanol/dichloromethane) to afford 2-cyclopropyl-oxazole-4-carboxylic acid [4-cyclopropyl-5-[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide 5c (34.0 mg; 0.06 mmol, 29.8%) as a white solid.

Provenance & Evidence