Methanol → HCID 178515272, compound

Participants

Reaction Conditions

Reaction Steps

(±)-5-({4-[6-(Methyloxy)pyridin-3-yl]phenyl}methyl)-2-(tetrahydro-2H-pyran-3-yl)-2,5-dihydro-3H-pyrazolo[4,3-c]pyrido[3,2-e]pyridazin-3-one (Example 14, 20 mg, 0.043 mmol) was dissolved in dichloromethane (3 mL), cooled to 0° C. and treated with iodotrimethylsilane (26 μL, 0.13 mmol, 3 equiv). After stirring for 15 minutes at 0° C., the mixture was warmed to ambient temperature and stirred for an additional 14 hours. The mixture was cooled to 0° C. treated with additional iodotrimethylsilane (26 μL, 0.13 mmol, 3 equiv) and after stirring for 15 minutes at 0° C., the mixture was warmed to ambient temperature and stirred for an additional 14 hours. The mixture was treated with methanol (1 mL), poured into water (10 mL) and extracted with ethyl acetate (2×20 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified via silica gel gradient chromatography (100:0 to 90: 10; dichloromethane:methanol), providing the titled compound as a deep red solid: high resolution mass spectrometry (ES+) m/z 455.1839 [(M+H)+; calculated for C25H23N6O3: 455.1826].

Provenance & Evidence