Sodium Thiosulfate → HCID 58902358, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-{[2-(5-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-4-yl]oxy}-N-[3-(2-pyrrolidin-1-ylethoxy)-5-(trifluoromethyl)phenyl]quinoline-3-carboxamide I-218 (0.500 g, 0.83 mmol) in DCM (20 mL) at 0° C. was added Dess-Martin periodinane (0.701 g, 1.65 mmol). The reaction mixture was allowed to stir at 0° C. overnight. Additional Dess-Martin periodinane (0.140 g, 0.32 mmol) was added and the reaction mixture was allowed to warm to rt until reaction was complete. Aq Na2S2O3 was added and the reaction mixture was allowed to stir at rt for 10 min before the addition of sat. aq. NaHCO3. The reaction mixture was extracted with DCM, concentrated, and purified by column chromatography to give 6-{[2-(5-methyl-1H-imidazol-2-yl)pyridin-4-yl]oxy}-N-[3-(2-pyrrolidin-1-ylethoxy)-5-(trifluoromethyl)phenyl]-quinoline-3-carboxamide I-409. 1H NMR (300 MHz, d6-DMSO, HCl salt) δ: 11.21 (s, 1H), 10.67-10.85 (br s, 1H), 9.45 (s, 1H), 9.11 (s, 1H), 8.71 (d, 1H), 8.29 (d, 1H), 8.13 (m, 1H), 8.04 (m, 1H), 7.94-7.91 (br s, 2H), 7.88-7.82 (m, 1H), 4.49-4.40 (m, 2H), 3.67-3.55 (m, 5H), 3.18-3.05 (m, 3H), 2.32 (s, 3H), and 2.08-1.84 (m, 5H). LCMS: (FA) ES+ 603.2, ES− 600.8.

Provenance & Evidence