N-(6-(6-Chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide → N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(4-fluoro-3-(morpholine-4-carbonyl)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Participants

Reaction Steps

Following the procedure described for N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-(3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide (TFA salt) (Example 22), N-(6-(6-chloro-5-(methylsulfonamido)pyridin-3-yl)-3-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (0.0650 g, 0.128 mmol) (Example 21) was reacted with 4-fluoro-3-(morpholine-4-carbonyl)phenylboronic acid (0.0390 g, 0.154 mmol, Combi-Blocks, San Diego, Calif.) at 90° C. for 3 h to afford the title compound as a yellow solid (0.058 g, 64%). MS (ESI, positive ion) m/z: 588 (M−TFA+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (s, 3H), 3.20 (s, 3H), 3.32 (s, 2H), 3.51-3.58 (m, 2H), 3.67 (br s, 4H), 7.45 (t, J=9.1 Hz, 1H), 7.80 (d, J=4.9 Hz, 1H), 7.99 (d, J=9.6 Hz, 1H), 8.04-8.09 (m, 1H), 8.31 (d, J=9.4 Hz, 1H), 8.48 (d, J=2.3 Hz, 1H), 8.93 (d, J=2.2 Hz, 1H), 9.93 (s, 1H), 10.28 (br s, 1H).

Provenance & Evidence