Sodium Hydroxide → N-(5-(2-Amino-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl)-2-chloropyridin-3-yl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a 4-mL vial was added N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (TFA salt) (Example 22) (0.025 g, 0.042 mmol), methanol (2.5 mL) and sodium hydroxide (0.250 mL, 2.5 mmol, 10 M). The mixture was stirred at 60° C. for 15 h. After cooling to rt, the mixture was neutralized with pH 4.8 buffer (Teknova, 3 M sodium acetate solution pH adjusted to 4.8). The solution was partially concentrated to remove the MeOH. The solution was filtered and the filtercake was washed with water (2×) and then dried under vacuum to afford the title compound as a yellow solid (0.016 g, 86%). MS (ESI, positive ion) m/z: 433 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.68 (s, 3H), 5.90 (s, 2H), 7.08-7.13 (m, 1H), 7.51-7.58 (m, 2H), 7.76-7.81 (m, 1H), 7.84 (d, J=9.2 Hz, 1H), 8.00 (d, J=8.0 Hz, 1H), 8.06 (s, 1H), 8.15 (d, J=2.2 Hz, 1H), 11.93 (br s, 1H).

Provenance & Evidence