2-Ethyl-4-methyl-1,3-oxazole-5-carboxylic acid → 2-(4-(4-(5-(2-Ethyl-4-methyloxazole-5-carboxamido)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

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Reaction Steps

The title compound was prepared analogous to Example 12, starting from methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (114 mg, 0.32 mmol) and 2-ethyl-4-methyloxazole-5-carboxylic acid (60.2 mg, 0.39 mmol). The crude product was purified on prep-HPLC to afford the title compound as off-white solid after drying (28 mg, 17% yield). HR/MS (M+H)+ found 476.2166. calc. 476.2185, RT: 2.76 (Condition L). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.55 (s, 1H), 8.98 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 8.01 (d, J=12.0 Hz, 2H), 7.95 (d, J=12.0 Hz, 1H), 7.43 (d, J=8.0 Hz, 2H), 3.91 (s, 2H), 2.86 (q, J=8.0 Hz, 2H), 2.36 (s, 2H), 2.25 (s, 2H), 2.09-1.90 (m, 8H), 1.36 (t, J=8.0 Hz, 3H).

Provenance & Evidence