HCID 68481210, compound → HCID 178486271, compound

Participants

Reaction Conditions

Reaction Steps

In a 2 dram vial was added 4-(6-chloro-3-cyanoimidazo[1,2-b]pyridazin-8-ylamino)-N-methylbenzenesulfonamide (0.025 g, 0.069 mmol) from (1b) and (trans)-cyclohexane-1,4-diamine (0.700 g, 6.13 mmol). The mixture was heated to 165° C. for 1 hour. Upon cooling, The mixture was diluted with CH2Cl2, then washed with water, dried over Na2SO4, filtered, concentrated and purified by HPLC to provide the titled compound (0.008 g, 26.4% yield). 1H NMR (400 MHz, MeOD) δ ppm 7.91-7.99 (1H, s), 7.82-7.88 (2H, m), 7.48-7.55 (2H, m), 6.42-6.56 (1H, s), 3.68-3.84 (1H, m), 3.06-3.21 (1H, m), 2.49-2.59 (3H, s), 2.23-2.38 (2H, m), 2.04-2.17 (2H, m), 1.48-1.66 (2H, m), 1.28-1.45 (2H, m). LC/MS, m/z 441 (M+1). HPLC Rt, 2.30 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Provenance & Evidence