Hydrochloric Acid → HCID 44125256, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL, round-bottomed flask was charged with N-(6-(6-chloro-5-(4-fluorophenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (150 mg, Example 12) and methanol (10 mL)-NaOH (10 N, 5 mL). The mixture was refluxed for 2 h. After the solution was cooled to 0° C., 10 N HCl was added until pH=7. The crude product was concentrated in vacuo. Purification by silica gel chromatography (10 to 50% MeOH/CH2Cl2), followed by further purification by preparative HPLC (Phenomenex Synergi 4μ MAX-RP 150×21.2 mm, 40 to 90% CH3CN/H2O, 0.1% TFA, over 15 min) (Phenomenex, Torrance, Calif.) provided N-(5-(2-aminoimidazo[1,2-b]pyridazin-6-yl)-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (20 mg, 5.0% yield) as a yellow solid. MS (ESI positive ion) m/z: 419 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 7.28 (t, J=8.80 Hz, 1H), 7.22-7.31 (m, 1H), 7.49 (s, 1H), 7.55 (d, J=9.19 Hz, 1H), 7.70-7.77 (m, 1H), 7.82-7.90 (m, 2H), 8.52 (d, J=2.15 Hz, 1H), 8.72 (d, J=2.15 Hz, 1H).

Provenance & Evidence