Sodium Iodide → Formic acid 6-(4-morpholinylmethyl)-N-[6-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide

Participants

Reaction Conditions

Reaction Steps

6-(Chloromethyl)-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-1H-indazol-4-yl}-2-pyridinecarboxamide (0.05 g, 0.09 mmol) was dissolved in MeCN (0.5 ml) and added to a vessel containing morpholine (0.1 mmol). DIPEA (0.026 ml, 0.15 mmol) and sodium iodide (0.015 g, 0.1 mmol) were then added and the mixture was heated to 70° C. for 18 hr. Potassium trimethylsilanolate (0.5 mmol, 0.063 g), dissolved in THF (0.25 ml) was then added and the mixture was heated at 50° C. for 24 hrs. After cooling the solution was quenched with aqueous MeCN (50:50, 1 ml) and neutralised. Solvent was removed in a blowdown unit. The sample was then dissolved in DMF (200 μl), Acetone (200 μl) and water (20 μl) and purified by Mass Directed AutoPrep HPLC (Method F). The solvent was removed in vacuo using the Genevac to give the title compound (5 mg).

Provenance & Evidence