Dimethylformamide → HCID 68350507, compound

Participants

Reaction Steps

A solution of (S)-4-((4,4-dimethylpyrrolidin-3-yl)amino)-6-(2-methoxypyridin-4-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide (12 mg, 0.024 mmol) in N,N-dimethylformamide (1 mL), was added BOP (10.2 mg, 0.024 mmol) and N,N-diisopropylethylamine (0.012 mL, 0.07 mmol). The mixture was stirred for 2 h. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19×250 mm, 5-μm particles; Guard Column: Waters XBridge C18, 19×10 mm, 5-μm particles; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10-mM ammonium acetate; Gradient: 25-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give the title compound (7 mg, 52% yield). 1H NMR (400 MHz, METHANOL-d4, Rotamer) δ 8.36 (s, 1H), 8.27 (d, J=3.7 Hz, 1H), 8.20 (d, J=5.9 Hz, 1H), 7.67-7.62 (m, 1H), 7.57 (dd, J=16.5, 1.8 Hz, 1H), 7.53 (d, J=3.1 Hz, 1H), 4.73 (t, J=5.9 Hz, 1H), 4.28-4.17 (m, 1H), 4.15 (d, J=6.4 Hz, 3H), 3.89 (d, J=3.5 Hz, 1H), 3.86-3.83 (m, 1H), 3.65-3.46 (m, 4H), 1.36-1.25 (m, 6H). MS (ES+) m/z: 448.2, 448.2 (M+H); LC retention time: 2.86 min (analytical HPLC Method I).

Provenance & Evidence