Trifluoroacetic acid methylene chloride → Trifluoroacetic acid

Participants

Reaction Steps

As a crude reaction mixture, N-(6-(6-(5-cyano-6-((2-(trimethylsilyl)ethoxy)methoxy)pyridin-3-yl)-[1,2,4]triazolo[4,3-a]-pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide was refluxed in TFA:DCM (1:1, 5 mL) for 30 min. The reaction was then concentrated and purified by preparative LCMS to provide the title compound, N-(6-(6-(5-cyano-6-hydroxypyridin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide as a TFA salt. The product was then dissolved in MeOH, treated 4M HCl in dioxane, and concentrated to dryness to provide the HCl salt of the title compound. 1H NMR (METHANOL-d4, 400 MHz): δ=8.80 (br. s., 1 H), 8.51 (d, J=2.5 Hz, 1 H), 8.13 (d, J=2.8 Hz, 1 H), 8.04 (d, J=9.6 Hz, 1 H), 7.79-7.96 (m, 3 H), 7.27 (d, J=7.8 Hz, 1 H), 1.83 (br. s., 1 H), 0.91 ppm (d, J=16.7 Hz, 4 H). ESI-MS:m/z 513.4 (M+H)+.

Provenance & Evidence