2-Aminopyridine → HCID 54765572, compound

Participants

Reaction Steps

A solution of (S)-2-(5-chloro-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-propionic acid (100 mg, 0.27 mmol), commercially available 2-aminopyridine (30 mg, 0.31 mmol), N-ethyl-N-dimethyaminopropyl carbodiimide hydrochloride (EDCI. HCl) (40 mg, 0.29 mmol), and N-hydroxybenzotriazole (HOBt) (56 mg, 0.29 mmol) in methylene chloride (5 mL) was stirred for 16 hours at 25° C. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue, upon silica gel flash chromatography using hexane-ethyl acetate gradiant elution, afforded (S)-2-(5-chloro-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-3-cyclohexyl-N-pyridin-2-ylpropionamide (36 mg, 30%), as a white solid. 1H NMR (DMSO-d6) δ: 10.86 (br. s., 1H), 8.34 (d, J=3.4 Hz, 1H), 8.00 (d, J=8.3 Hz, 1H), 7.77 (t, J=7.6 Hz, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.23 (d, J=7.3 Hz, 1H), 7.05-7.16 (m, 2H), 5.10 (d, J=6.8 Hz, 1H), 4.43 (d, J=19.1 Hz, 1H), 4.06 (d, J=19.1 Hz, 1H), 3.83 (br. s., 2H), 1.51-1.87 (m, 7H), 0.75-1.30 (m, 6H).

Provenance & Evidence