Trifluoroacetic acid → HCID 89995491, compound

Participants

Reaction Steps

A solution of 2-(1-ethyl-1H-pyrazol-4-yl)-8-(((3S,4S)-4-methylpyrrolidin-3-yl)amino)imidazo[1,2-b]pyridazine-7-carboxamide, 2 TFA (0.020 g, 0.034 mmol), 6-bromonicotinonitrile (0.013 g, 0.069 mmol) and Hunig's Base (0.030 ml, 0.172 mmol) in DMF (0.3 ml) in a reaction vial was stirred at 100° C. for 5 h. The crude material was purified via preparative LC/MS (Method A). Fractions containing the desired product were combined and dried via centrifugal evaporation to afford the title compound of Example 1 (10.0 mg, 0.022 mmol, 63.8% yield). 1H NMR (500 MHz, deuterated 1:1 methanol:chloroform) δ 8.53 (br. s., 1H), 8.51 (s, 1H), 8.15 (s, 1H), 8.11 (s, 1H), 8.07 (s, 1H), 7.84 (d, J=8.9 Hz, 1H), 6.69 (d, J=7.4 Hz, 1H), 6.32 (br. s., 1H), 4.43 (q, J=7.3 Hz, 3H), 4.19 (br. s., 1H), 4.12-3.91 (m, 2H), 3.70-3.57 (m, 1H), 3.06 (d, J=12.9 Hz, 1H), 1.72 (t, J=7.4 Hz, 3H), 1.43 (d, J=6.9 Hz, 3H). LC/MS (Method F): m/z 456.20 ([M+H]+), Rt. 1.310 min.

Provenance & Evidence