Hydrochloric Acid → (E)-3-(4-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzamido)propanoic acid

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Reaction Steps

Compound 7a (0.20 g, 0.36 mmol) was suspended in THF/MeOH (4:1 v/v, 5 mL), and treated with 1 N LiOH solution (2.0 mL). The resulting mixture was stirred at rt for 3 h, and treated with water. The pH of the mixture was adjusted to ca. pH 5 using 1 N HCl solution. The resulting mixture was extracted with DCM (2×200 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue obtained was washed with MeOH, and dried under high vacuum to give the title compound 44 as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.14 (d, J=8.6 Hz, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.97-8.03 (m, 3H), 7.94 (d, J=15.6 Hz, 1H), 7.76-7.86 (m, 3H), 7.64-7.76 (m, 3H), 7.46-7.55 (m, 1H), 6.15 (d, J=5.6 Hz, 1H), 4.08 (d, J=3.4 Hz, 4H), 4.01 (d, J=3.4 Hz, 4H), 3.74 (t, J=5.9 Hz, 2H), 2.70 (t, J=5.9 Hz, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C31H28N6O4: 549.2 (M+H). Found 549.2.

Provenance & Evidence