Tetrahydrofuran → tert-Butyl 4-(5-(2-(2-hydroxyethyl)-8-morpholinoimidazo[1,2-b]pyridazin-3-yl)pyridin-2-yl)piperazine-1-carboxylate

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Reaction Conditions

Reaction Steps

Compound 28e (260 mg, 0.471 mmol) was placed in an 8 mL vial equipped with a stir bar and then the vial was evacuated and backflushed with argon. Dry THF (4 mL) was added and then the solution was cooled to 0° C. in an ice bath. 1 M LiAlH4 in THF (0.471 mL, 0.471 mmol) was added and then the ice bath was removed and the reaction was allowed to warm to rt. The reaction was stirred at rt for 20 min and then poured into saturated NH4Cl solution (20 mL). DCM (20 mL) was added and then the mixture was filtered. The filter cake was washed with DCM (2×10 mL) and then the organic phase was separated. The aqueous layer was extracted with DCM (3×10 mL) and then the organic extracts were combined, dried over Na2SO4, and filtered. The solvent was removed under reduced pressure. The crude product was chromatographed on a 12 g SiO2 pre-packed column eluting with 0-100% ACN/DCM to afford compound 28f. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.38 (d, J=2.2 Hz, 1H), 8.00 (d, J=5.4 Hz, 1H), 7.81 (dd, J=8.8, 2.4 Hz, 1H), 6.78 (d, J=8.8 Hz, 1H), 6.10 (d, J=5.6 Hz, 1H), 3.97-4.07 (m, 3H), 3.92 (s, 8H), 3.52-3.65 (m, 8H), 3.05 (t, J=4.6 Hz, 2H), 1.50 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C26H35N7O4: 510.3 (M+H). Found: 510.2.

Provenance & Evidence