Methyl morpholine oxide → 1-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanone

Participants

Reaction Conditions

Reaction Steps

A solution of 1-{3-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanol (0.77 g, 1.96 mmol) dissolved in CH2Cl2 (20 mL) is cooled to 0° C., treated with NMO (0.34 g, 2.94 mmol) and TPAP (34 mg, 0.098 mmol). The reaction is stirred at 0° C. for 10 min, then at RT for 4 h. It is filtered through silica gel, washed with EtOAc. Purification of the crude material by silica gel chromatography gives the title compound (0.63 g, 1.61 mmol, 82%) as a yellow solid. 1H NMR (CDCl3): δ 0.92 (t, J=7.5 Hz, 3H), 0.93 (t, J=7.5 Hz, J=7.5 Hz, 3H), 1.80-1.95 (m, 4H), 2.43 (s, 3H), 2.45 (s, 3H), 2.48 (s, 3H), 3.12 (s, 3H), 3.34-3.46 (m, 1H), 6.75 (s, 1H), 6.83 (t, J=7.0 Hz, 1H), 7.67 (dd, J=7.1, 1.4 Hz, 1H), 7.91 (dd, J=7.1, 1.4 Hz, 1H) ppm. ES-MS (m/z): calcd for C23H27N5O (M+H)+: 390.5. found: 390.2.

Provenance & Evidence