6-Methylanthranilic acid → 2-[2-(2-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-pyridin-3-yl]-5-methyl-4H-benz[d][1,3]oxazin-4-one

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Reaction Conditions

Reaction Steps

A solution of compound D (164.7 mg, 0.50 mmol) in CH3CN (2.0 mL) was treated with N,N′-carbonyldiimidazole (CDI, 81.1 mg, 0.50 mmol) at 65° C. under N2 for 1 h. 6-Methylanthranilic acid (75.6 mg, 0.50 mmol) was added at 25° C., and the mixture was heated at 65° C. overnight. Additional CDI (81.1 mg, 0.50 mmol) was added and the mixture was heated at 65° C. for 8 h. The crude mixture was purified by C18 reverse phase chromatography to provide compound 52 as colorless gum (120.0 mg, 54%). 1H-NMR (400 mHz, CDCl3) δ 8.29 (dd, 1H, J=5.2 Hz, J=2.0 Hz), 8.25 (dd, 1H, J=7.6 Hz, J=2.0 Hz), 7.66 (t, 1H, J=7.8 Hz), 7.50 (d, 1H, J=7.6 Hz), 7.31 (d, 1H, J=7.6 Hz), 7.01 (dd, 1H, J=7.4 Hz, J=5.0 Hz), 4.62 (m, 2H), 3.94 (m, 2H), 3.78 (m, 2H), 3.62 (m, 8H), 3.51 (m, 2H), 3.34 (s, 3H), 2.82 (s, 3H). ESMS: 445.0 [M+H]+, 467.0 [M+Na]+.

Provenance & Evidence