Diisopropylethylamine → 5-(3-Hydroxyazetidine-1-carbonyl)-4'-methyl-N-((2-methylpyrimidin-5-yl)methyl)biphenyl-3-carboxamide

Participants

Reaction Steps

To a mixture of 5-(3-hydroxyazetidine-1-carbonyl)-4′-methylbiphenyl-3-carboxylic acid (350 mg, 1.1 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (430 mg, 2.2 mmol), 1-hydroxybenzotriazole hydrate (170 mg, 1.1 mmol), CH2Cl2 (50 mL) were added (2-methylpyrimidin-5-yl)methanamine (210 mg, 1.7 mmol) and N,N-diisopropylethylamine (0.39 mL, 2.2 mmol). The mixture was stirred at room temperature for 4 h, and then washed with water and aq. Na2CO3 solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by preparative HPLC (100×21.2 mm C18 column, 20-60% MeCN/water[10 mM Et2NH]) to yield a white solid.

Provenance & Evidence