Triethylamine → HCID 178425188, compound

Participants

Reaction Steps

To a solution of (S)-4-(1-phenoxyethyl)benzoic acid (121 mg, 0.5 mmol) in dichloromethane (20 mL) was added 1H-benzo[d][1,2,3]triazol-1-ol (135 mg, 1 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (190 mg, 1 mmol) and triethylamine (252 mg, 2.5 mmol), and stirred at room temperature for 0.5 hour, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (152 mg, 1 mmol) was added and stirred for 4 hours. To the reaction mixture was added water (20 mL), extracted with dichloromethane (20 mL) two times, combined and concentrated the organic layers, the residue was purified by chromatography with dichloromethane/methanol=20:1 to afford (S)—N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-phenoxyethyl)benzamide (150 mg, 80%). LRMS (M+H+) m/z: calcd for 376.18. found 376. HPLC Purity (214 nm): 96%. 1H NMR (300 MHz, DMSO-d6): δ 11.45 (s, 1H), 8.30 (t, J=5.1 Hz, 1H), 7.79 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H), 7.18 (t, J=7.2 Hz, 2H), 6.88-6.81 (m, 3H), 5.84 (s, 1H), 5.52 (q, J=6.3 Hz, 1H), 4.27 (d, J=4.8 Hz, 2H), 2.15 (s, 3H), 2.10 (s, 3H), 1.54 (d, J=6.6 Hz, 3H).

Provenance & Evidence