P-Toluenesulfonylhydrazide → tert-Butyl 4-(8-morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)ethyl)imidazo[1,2-b]pyridazin-3-yl)benzoate

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Reaction Steps

A mixture of compound 60a (60.0 mg, 0.112 mmol), 4-methylbenzenesulfonohydrazide (104 mg, 0.558 mmol) and sodium acetate (46.2 mg, 0.558 mmol) in 3.3 mL of 10:1 DME/water was refluxed for 4 h. After cooling to rt, the mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (0:1-3:2 EtOAc/DCM) to afford compound 60b as a colorless oil. 1H-NMR (CDCl3; 400 MHz) δ 8.05 (d, J=8.6 Hz, 2H), 7.96 (d, J=5.6 Hz, 1H), 7.57 (d, J=8.6 Hz, 2H), 7.15 (d, J=7.6 Hz, 1H), 6.76 (d, J=7.6 Hz, 1H), 6.07 (d, J=5.6 Hz, 1H), 3.96-4.03 (m, 4H), 3.89-3.96 (m, 4H), 3.15-3.30 (m, 4H), 2.83 (t, J=6.3 Hz, 2H), 2.69 (t, J=6.3 Hz, 2H), 1.82-1.91 (m, 2H), 1.73-1.82 (m, 2H), 1.61 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C32H37N5O3, 540.3 (M+H). found 540.5.

Provenance & Evidence