Hydrochloric Acid → 3-(8-(5,6-Dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid

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Reaction Steps

Ethyl 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoate (150 mg, 358 μmol) was dissolved in dioxane (18 mL). To this was added a solution of LiOH (85.6 mg, 3.58 mmol) in water (9 mL). The mixture was stirred for 4 h, acidified with 1N HCl, and concentrated in vacuo to give the crude acid which was recrystallized from isopropyl alcohol and methanol to give 3-(8-(5,6-dimethoxypyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (123 mg, 314 μmol, 88%) as a light brown powder. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.97 (s, 1H) 8.60 (s, 1H) 8.52 (s, 1H) 8.17-8.30 (m, 2H) 8.05 (d, J=7.55 Hz, 1H) 7.60-7.72 (m, 2H) 7.41 (d, J=8.31 Hz, 1H) 7.12 (d, J=8.31 Hz, 1H) 4.05 (s, 3H) 3.76 (s, 3H); LC/MS: 391.8 [MH]+.

Provenance & Evidence