Ethyl Acetate → 3-[(5,5-Dioxido-3,4-dihydro-2H-1,5-benzoxathiepin-8-yl)oxy]-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (0.15 g, 0.47 mmol), 8-fluoro-3,4-dihydro-2H-1,5-benzoxathiepine 5,5-dioxide (103 mg, 0.47 mmol) and potassium carbonate (131 mg, 0.95 mmol) in acetonitrile (5 mL) was stirred in a microwave reactor at 160° C. for 5 hours. The mixture was reduced in vacuo and ethyl acetate (50 mL) and water (50 mL) were added. The aqueous layer was re-extracted into ethyl acetate (50 mL) and the combined organics washed with water (50 mL), brine (50 mL), dried (MgSO4), filtered and reduced in vacuo to give a golden oil. The oil was chromatographed on silica, eluting with 40-100% ethyl acetate in isohexane, to give the desired compound as a white foam (84 mg). 1H NMR δ (CDCl3): 1.34 (d, 3H), 2.39-2.47 (m, 2H), 2.56 (s, 3H), 3.34-3.37 (m, 2H), 3.41 (s, 3H), 3.49-3.61 (m, 2H), 4.24-4.27 (m, 2H), 4.58-4.65 (m, 1H), 6.76 (d, 1H), 6.85-6.88 (m, 2H), 7.16 (t, 1H), 7.35 (t, 1H), 7.94 (d, 1H), 8.14 (s, 1H), 8.30 (s, 1H), 9.53 (s, 1H); m/z 514 (M+H)+

Provenance & Evidence