Diisopropylethylamine → HCID 68291496, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 2, 0.27 g, 0.99 mmol) in DMF (1 mL) was added (±)-cis-benzyl 3-amino-4-methoxypyrrolidine-1-carboxylate (Intermediate 12, 0.3 g, 1.18 mmol) and DIPEA (0.37 mL, 2.1 mmol). The mixture was heated at 80° C. overnight. The mixture was then poured into water, stirred for 1 h, and filtered. The solid was rinsed with water, dried under vacuum. The solid was dissolved in acetonitrile (5 mL) and iodotrimethylsilane (0.590 g, 2.95 mmol) was added at 0° C., then the mixture was stirred at rt for 3 h, diluted with ether and stirred at rt for 1 h. The solids were filtered and rinsed with ether and dried to afford the hydroiodide salt of 6-bromo-4-((cis-4-methoxypyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide (0.4 g, 84% yield) as brown solid. 1H NMR (400 MHz, METHANOL-d4) δ 8.17 (s, 1H), 7.70 (d, J=1.5 Hz, 1H), 7.07 (s, 1H), 4.97-4.88 (m, 2H), 4.56 (br. s., 1H), 4.16-4.09 (m, 1H), 3.67 (dd, J=11.4, 7.7 Hz, 1H), 3.53-3.50 (m, 3H), 3.50-3.45 (m, 1H), 3.40-3.34 (m, 1H), 3.11 (dd, J=11.6, 8.5 Hz, 1H); MS (ES+) m/z: 353.1, 354.0 (M+H); LC retention time: 2.01 min (analytical HPLC Method J).

Provenance & Evidence