1-Hydroxybenzotriazole → 3-Bromo-N-((2-methylpyrimidin-5-yl)methyl)-5-(pyrrolidine-1-carbonyl)benzamide

Participants

Reaction Steps

Into a round-bottom flask were charged 3-bromo-5-(pyrrolidine-1-carbonyl)benzoic acid (340 mg, 1.0 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.39 g, 2.0 mmol), 1-hydroxybenzotriazole (0.30 g, 2.2 mmol), N,N-diisopropylethylamine (0.2 g, 1.5 mmol), methylene chloride (10 mL), 4-dimethylaminopyridine (5 mg, 0.04 mmol), and (2-methylpyrimidin-5-yl)methanamine (240 mg, 1.5 mmol). The mixture was stirred at room temperature overnight, and then diluted with CH2Cl2. The separated organic phase was washed with aq. Na2HPO4, brine, and dried over Na2SO4, and concentrated. The residue was purified via flash chromatography to afford the desired product as an oil. LC-MS: 404.8 [M+1]+; 1H NMR (400 MHz, CDCl3): 8.68 (s, 2H), 7.95 (t, J=1.6 Hz, 1H), 7.76 (t, J=1.3 Hz, 1H), 7.74-7.71 (m, 1H), 7.61 (t, J=1.5 Hz, 1H), 4.57 (d, J=5.8 Hz, 2H), 3.56 (t, J=6.8 Hz, 2H), 3.37 (t, J=6.4 Hz, 2H), 2.73 (s, 3H), 1.96-1.89 (m, 4H).

Provenance & Evidence