Triethylamine → HCID 11712784, compound

Participants

Reaction Steps

A mixture of 6-bromo-2-(4-methoxyphenyl)benzoxazole carboxylic acid (86 mg, 0.25 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (94 mg, 0.49 mmol), 1-hydroxybenzotriazole (67 mg, 0.49 mmol) and 3-amino-9-methyl-9-azabicyclo[3.3.1]nonane dihydrochloride (67 mg, 0.30 mmol) in DMF (5 mL) was stirred for 10 min at room temperature, then triethylamine (0.100 mL, 0.99 mmol) was added. The resulting reaction mixture was stirred at room temperature for 18 h. The mixture was diluted with ethyl acetate and then washed with a saturated solution of sodium bicarbonate. The aqueous layer was further extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (2×100 mL), dried (Na2SO4), filtered and concentrated. The crude material was purified by column chromatography (silica gel, 90:9:1 ethyl acetate/methanol/concentrated ammonium hydroxide) to afford N-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-6-bromo-2-(4-methoxyphenyl)benzoxazole-4-carboxamide (32 mg, 27%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 8.99 (br s, 1H), 8.30 (d, J=1.8 Hz, 1H), 8.17 (d, J=8.8 Hz, 2H), 7.81 (d, J=1.8 Hz, 1H), 7.10-7.05 (m, 2H), 4.60-4.55 (m, 1H), 3.93 (s, 3H), 3.25-3.15 (m, 2H), 2.70-2.55 (m, 5H), 2.40-2.00 (m, 3H), 1.70-1.20 (m, 5H); MS (ESI+) m/z 484 (M+H); HPLC>99% (AUC), tR=15.30 min.

Provenance & Evidence