Pyridine → 3-[6-(Azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-pyridin-2-yl-benzamide

Participants

Reaction Steps

1-Chloro-N,N,2-trimethyl-prop-1-en-1-amine (0.077 mL, 0.58 mmol) was added to a solution of 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid (Intermediate 30) (200 mg, 0.49 mmol) in DCM (5 mL) and stirred at ambient temperature for 50 minutes. 2-Amino-pyridine (93 mg, 0.98 mmol) and pyridine (0.080 mL, 0.98 mmol) were added and the reaction stirred for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate (40 mL), washed with water (10 mL), and brine (10 mL), dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with a gradient of 0-100% methanol in DCM to afford the product (112 mg, 47%). 1H NMR δ (300 MHz, CDCl3) 2.12-2.26 (m, 1H), 2.35 (quintet, 2H), 2.53-2.66 (m, 1H), 2.93 (s, 3H), 3.34-3.57 (m, 2H), 4.25 (t, 2H), 4.70 (t, 2H), 4.93 (t, 1H), 6.97 (s, 1H), 7.08 (t, 1H), 7.22 (s, 1H), 7.38 (d, 1H), 7.45 (s, 1H), 7.75 (t, 1H), 8.11 (d, 1H), 8.29 (d, 1H), 8.33 (q, 2H), 8.68 (s, 1H); m/z 488 (M+H)+.

Provenance & Evidence