Diisopropylethylamine → HCID 68358957, compound

Participants

Reaction Conditions

Reaction Steps

Hunig's base (1.27 mL, 7.29 mmol) was added to a solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Preparation 5, 625 mg, 2.277 mmol) and (1S,3R)-methyl 3-amino-1,2,2-trimethylcyclopentanecarboxylate (464 mg, 2.505 mmol) in NMP (5692 n1). The reaction was heated at 90° C. for 14 hrs. The reaction was cooled to room temperature and diluted with ethyl acetate (20 ml). The ethyl acetate solution was washed with water (3×10 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure to give a light yellow oil. The crude product was chromatographed on the silica gel column eluted with 0-50% ethyl acetate in hexane to afford the title compound (583 mg, 1.308 mmol, 57.5% yield) as a white solid. LC/MS found [M+H]+=425.1. 1H NMR (400 MHz, MeOD) δ ppm 8.13 (1 H, s), 7.60-7.66 (1 H, m), 6.88-6.95 (1 H, m), 4.43-4.52 (1 H, m), 3.71 (3 H, s), 2.62-2.71 (1 H, m), 2.31-2.39 (1 H, m), 1.65-1.76 (1 H, m), 1.55-1.64 (1 H, m), 1.32 (3 H, s), 1.09 (3 H, s), 0.98 (3 H, s).

Provenance & Evidence