Carbonate Ion → Methyl 3-[5-(azetidine-1-carbonyl)pyrazin-2-yl]oxy-5-[(3R)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-hydroxy-5-[(3R)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 12) (265 mg, 1 mmol), azetidin-1-yl-(5-chloropyrazin-2-yl)methanone (Intermediate 32) (298 mg, 1.5 mmol) and polymer supported-carbonate (860 mg, 2.5 mmol) in DMA (5 mL) was stirred at 100° C. for 2 hours. The mixture was filtered and the DMA was removed under reduced pressure. The residue was purified by flash chromatography on silica eluting with 20-100% ethyl acetate in isohexane then 10% methanol in DCM to afford the product (292 mg, 68%). 1H NMR δ (300 MHz, CDCl3) 2.13-2.27 (m, 1H), 2.31-2.44 (m, 2H), 2.53-2.66 (m, 1H), 2.94 (s, 3H), 3.35-3.58 (m, 2H), 3.90 (s, 3H), 4.26 (t, 2H), 4.68 (t, 2H), 4.93 (t, 1H), 7.14 (s, 1H), 7.46 (s, 1H), 7.60 (s, 1H), 8.31 (s, 1H), 8.84 (s, 1H); m/z 427 (M+H)+

Provenance & Evidence