Dimethylformamide → HCID 68291185, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-((4,4-dimethylpyrrolidin-3-yl)amino)-6-(1-ethyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (38 mg, 0.103 mmol) in DMF (0.3 mL), was added 6-bromonicotinonitrile (20.8 mg, 0.114 mmol), DIPEA (0.06 mL, 0.31 mmol), The mixture was heated at 100° C. overnight. The reaction was cooled to rt, and purified via preparative HPLC to afford 15 mg of the. The product was subjected to chiral SFC chromatography to afford the title compound (1.1 mg, 2% yield) as a single enantiomer. 1H NMR (400 MHz, METHANOL-d4) δ 8.40 (d, J=1.8 Hz, 1H), 8.16 (s, 1H), 8.02 (s, 1H), 7.87-7.83 (m, 2H), 7.76 (dd, J=8.9, 2.3 Hz, 1H), 7.21 (d, J=1.8 Hz, 1H), 6.65 (d, J=8.8 Hz, 1H), 4.22 (q, J=7.3 Hz, 2H), 3.70-3.54 (m, 3H), 3.51-3.49 (m, 1H), 3.18-3.14 (m, 1H), 1.51 (t, J=7.3 Hz, 3H), 1.32 (d, J=9.7 Hz, 6H). MS (ES+) m/z: 470.32 (M+H); LC retention time: 3.50 min (analytical HPLC Method H).

Provenance & Evidence