Diisopropylethylamine → (E)-Methyl 3-(4-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzamido)propanoate

Participants

Reaction Steps

To a solution of Compound 40 (0.21 g, 0.36 mmol, Example 5) in DMF (3 mL) was added methyl 3-aminopropanoate (0.12 g, 0.89 mmol), HATU (0.20 g, 0.53 mmol) and DIEA (0.37 mL, 2.1 mmol). The resulting mixture was stirred at rt for 16 h and poured into water (20 mL). The aqueous layer was extracted with DCM (2×20 mL). The combined organic layers were dried over MgSO4 and filtered. Upon removal of the solvent, the resultant residue was purified by flash chromatography on silica gel (40-100% EtOAc/heptane) to give compound 7a as a red solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.12 (d, J=8.8 Hz, 1H), 8.07 (d, J=8.6 Hz, 1H), 7.92-8.03 (m, 4H), 7.84 (d, J=8.6 Hz, 2H), 7.78 (d, J=8.1 Hz, 1H), 7.65-7.76 (m, 3H), 7.46-7.54 (m, 1H), 6.97 (t, J=6.0 Hz, 1H), 6.13 (d, J=5.6 Hz, 1H), 4.06-4.13 (m, 4H), 3.96-4.03 (m, 4H), 3.76-3.83 (m, 2H), 3.75 (s, 3H), 2.71 (t, J=5.9 Hz, 2H).

Provenance & Evidence