Reaction Steps
A solution of 2-(1-ethyl-1H-pyrazol-4-yl)-8-(((3S,4S)-4-ethylpyrrolidin-3-yl)amino)imidazo[1,2-b]pyridazine-7-carboxamide, TFA (11 mg, 0.023 mmol), 1-cyanocyclopropanecarboxylic acid (5.07 mg, 0.046 mmol), HATU (13.00 mg, 0.034 mmol) and DIPEA (0.020 ml, 0.114 mmol) in DMF (0.4 ml) was stirred at room temperature for 45 min. The crude material was purified via preparative LC/MS (preparative LC/MS Method A). Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compound of Example 36 (8 mg, 0.017 mmol, 76% yield). 1H NMR (500 MHz, methanol-d4, 2 rotamers) δ 8.52 (d, J=7.4 Hz, 2H), 8.17 (s, 1H), 8.12 (d, J=2.5 Hz, 2H), 8.10 (s, 1H), 8.05 (d, J=5.0 Hz, 2H), 6.20 (t, J=4.2 Hz, 1H), 6.19-6.16 (m, 1H), 4.57 (dd, J=11.4, 5.0 Hz, 1H), 4.51-4.46 (m, 1H), 4.45-4.38 (m, 6H), 4.07-4.02 (m, 2H), 3.97 (t, J=10.9 Hz, 1H), 3.59 (t, J=11.4 Hz, 1H), 2.84-2.75 (m, 1H), 2.73-2.65 (m, 1H), 2.03-1.98 (m, 1H), 1.96-1.81 (m, 4H), 1.81-1.73 (m, 4H), 1.73-1.63 (m, 8H), 1.62-1.58 (m, 1H), 1.21 (t, J=7.4 Hz, 3H), 1.18 (t, J=7.4 Hz, 3H). HPLC/LCMS (Method F): m/z 461.20 ([M+H]+), Rt. 1.30 min.
