Sodium Hydroxide → 4-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid

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Reaction Steps

To a stirred solution of methyl 4-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (0.135 g, 0.333 mmol) in dioxane (20 mL) and H2O (10 mL) was added NaOH (133 mg, 3.33 mmol) at 25° C. After 2 h the mixture was washed with ether (10 mL) and the aqueous layer was adjusted to pH=4 with concentrated HCl, then it was concentrated and filtered. The solid was washed with ether and dried to afford 4-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (0.101 g, 77%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 9.98 (s, 1H), 8.57 (s, 1H), 8.24 (s, 1H), 8.11-8.03 (m, 4 h), 7.69 (s, 1H), 7.43 (d, 1H, J=8.4 Hz), 7.13 (d, 1H, J=8.7 Hz), 4.04 (s, 3H), 3.79 (s, 3H). LC-MS: [M+H]+, 391.9, tR=1.454 min, HPLC: 98.08% at 214 nm, 95.71% at 254 nm, tR=3.628 min.

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