Trifluoroacetic acid → 6-(3-Amino-1,2-benzisoxazol-5-yl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

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Reaction Steps

To a solution of 5-(8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)benzo[d]isoxazol-3-amine from (1c) was added TFA (1 mL) and the solution stirred at RT for 1 hour. The reaction solution was concentrated in vacuo, diluted with methanol and purified by preparative HPLC to provide the titled compound (13.20 mg, 70%). 1H NMR (500 MHz, CD3OD) δ ppm 8.3 (1H, s), 8.21 (1H, d=2.2 Hz), 8.11 (1H, m), 7.97 (1H, m), 7.52 (4H, m), 7.3 (1H, m), 7.1 (1H, m), 7.07 (1H, d, J=8.8 Hz). LC/MS, m/e 343 (M+1). HPLC Rt, 2.63 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