2-Aminopyridine → HCID 54765575, compound

Participants

Reaction Steps

A solution of (S)-2-(5-chloro-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-4-methyl-pentanoic acid (100 mg, 0.27 mmol) (Example 22, Step 1c), commercially available 2-aminopyridine (33 mg, 0.36 mmol), N-ethyl-N-dimethyaminopropyl carbodiimide hydrochloride (EDCI. HCl) (63 mg, 0.32 mmol), and N-hydroxybenzotriazole (HOBt) (44 mg, 0.32 mmol) in methylene chloride (1 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 gradient elution, afforded (S)-2-(5-chloro-3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-4-methyl-pentanoic acid pyridin-2-ylamide (55 mg, 45%), as a white solid. 1H NMR (DMSO-d6) δ: 10.88 (s, 1H), 8.34 (d, J=3.4 Hz, 1H), 8.01 (d, J=7.8 Hz, 1H), 7.77 (t, J=7.8 Hz, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.23 (d, J=7.8 Hz, 1H), 7.13 (d, J=7.8 Hz, 2H), 5.08 (d, J=6.8 Hz, 1H), 4.43 (d, J=18.6 Hz, 1H), 4.06 (d, J=19.1 Hz, 1H), 3.82 (br. s., 2H), 1.78-1.94 (m, 1H), 1.61-1.74 (m, 1H), 1.47 (br. s., 1H), 0.94 (t, J=4.9 Hz, 6H).

Provenance & Evidence