Trifluoroacetic acid → HCID 70982784, compound

Participants

Reaction Steps

N-(4-((trans)-3-amino-2-methyl-1-piperidinyl)-3-pyridinyl)-2-(3-fluoro-2-pyridinyl)imidazo[1,5-b]pyridazin-7-amine (enantiomer 1) (Example 54). tert-Butyl (1-(3-((2-(2,6-difluorophenyl)imidazo[1,5-b]pyridazin-7-yl)amino)pyridin-4-yl)-2-methylpiperidin-3-yl)carbamate (first eluting enantiomer) (53 mg, 0.09 mmol) in 2 mL of DCM was treated with 0.5 mL of TFA and stirred at RT for 1 h. Volatiles were removed under reduced pressure. The residue was treated with 10 mL of 1 N NaOH, and the mixture was extracted with 3×15 mL of EtOAc. The combined organic extracts were washed with 2×5 mL of water followed by 2×5 mL of brine, dried over sodium sulfate and concentrated to give the title compound (39 mg, 96% yield) as an orange amorphous solid. MS (ESI, pos. ion) m/z: 436.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.47 (1 H, s), 8.00-8.17 (2 H, m), 7.63 (1 H, tt, J=8.5, 6.5 Hz), 7.39 (1 H, s), 7.30 (2 H, m), 7.16 (1 H, d, J=5.1 Hz), 6.70 (1 H, d, J=9.4 Hz), 3.37 (3 H, br.), 2.78 (2 H, m), 2.56 (1 H, m), 2.36 (1 H, m), 1.76 (1 H, m), 1.59 (2 H, m), 1.23 (1 H, m), 0.84 (3 H, d, J=6.3 Hz). 19F NMR (376 MHz, DMSO-d6) δ ppm −113.35. The relative stereochemistry was confirmed by 1H-NMR studies.

Provenance & Evidence