Sodium Hydroxide → 4-(3-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)-2-methoxybenzoic acid

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Reaction Conditions

Reaction Steps

A mixture of methyl 4-(3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)-2-methoxybenzoate (100 mg, 0.18 mmol) and NaOH (100 mg, 2.5 mmol) in 1,4-dioxane (5 mL) and water (5 mL) was stirred for 2 h at 50° C. The mixture was concentrated and adjusted to pH=2 with 3M HCl. The precipitate was filtered and the solid was washed with MeOH (1 mL) and dichloromethane (1 mL) to give 4-(3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)-2-methoxybenzoic acid (24 mg, 25%) as a brown solid. 1H NMR (300 MHz, DMSO): δ 10.62 (s, 1H), 10.01 (s, 1H), 8.63 (s, 1H), 8.53 (s, 1H), 8.26-8.21 (m, 2H), 8.09 (d, 1H, J=7.5 Hz), 7.75-7.67 (m, 4 h), 7.50 (dd, 1H, J1=8.4 Hz, J2=1.8 Hz), 7.41 (d, 1H, J=8.4 Hz), 7.10 (d, 1H, J=8.4 Hz), 4.03 (s, 3H), 3.84 (s, 3H), 3.77 (s, 3H). LC-MS: [M+H]+, 541, tR=1.548 min, HPLC: 95.24% at 214 nm, 95.03% at 254 nm, tR=7.943 min.

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