2-Chloro-6-methylbenzene-1-sulfonyl chloride → HCID 44125258, compound

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Reaction Conditions

Reaction Steps

To a 50 mL, round-bottomed flask was added N-(6-(5-amino-6-chloropyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide from Step 2 (30 mg, 99 μmol), 2-chloro-6-methylbenzenesulfonyl chloride (149 μl, 661 μmol, Alfa Aesar, Ward Hill, Mass.), and pyridine (5 mL). The reaction mixture was stirred at 25° C. for 15 h and concentrated in high vacuum. Purification by silica gel chromatography (5 to 20% MeOH/CH2Cl2 provided N-(6-(6-chloro-5-(2-chloro-6-methylphenylsulfonamido)pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (20 mg, 41% yield) as an off-white solid. MS (ESI positive ion) m/z: 491 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.13 (s, 3H), 2.59 (s, 3H), 7.37 (d, J=7.03 Hz, 1H), 7.50 (q, J=7.53 Hz, 2H), 7.83 (d, J=9.54 Hz, 1H), 8.13 (d, J=9.03 Hz, 1H), 8.31 (s, 1H), 8.38 (s, 1H), 8.91 (s, 1H), 10.71 (s, 1H), 10.99 (s, 1H).

Provenance & Evidence