Diisopropylethylamine → HCID 178481739, compound

Participants

Reaction Steps

To a solution of 4-(4-methoxybenzyloxy)-1-methyl-3-(4-(2-oxopiperidin-1-yl)phenyl)-1H-pyrazole-5-carboxylic acid T-22 (180 mg, 0.42 mmol) in N,N-dimethylformamide (4 mL) were added 3,4-diaminobenzonitrile (66 mg, 0.5 mmol), HATU (204 mg, 0.54 mmol) and diisopropylethylamine (0.22 mL, 1.3 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. The residue was purified by flash chromatography. To the purified fraction (155 mg, 0.28 mmol) was added acetic acid (4 mL). The reaction mixture was heated in a microwave reactor at 150° C. for 55 minutes. Solvent was evaporated under reduced pressure. To the residue was added trifluoroacetic acid (4 mL). The reaction mixture was heated in a microwave reactor at 120° C. for 30 minutes. Solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography to afford the desired 2-(4-hydroxy-1-methyl-3-(4-(2-oxopiperidin-1-yl)phenyl)-1H-pyrazol-5-yl)-1H-benzo[d]imidazole-5-carbonitrile T-23 (110 mg, 0.27 mmol).

Provenance & Evidence