Sodium Iodide → Formic acid N-(6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-(4-morpholinylmethyl)-1,3-thiazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-(Chloromethyl)-N-[6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg, 0.078 mmol) was dissolved in MeCN (0.5 ml) and added to morpholine (0.1 mmol). DIPEA (0.026 ml, 0.15 mmol) was added followed by sodium iodide (0.015 g, 0.1 mmol) and the solutions was stirred for 18 hr at 70° C. Potassium trimethylsilanolate (64 mg, 0.5 mmol) was dissolved in THF (0.25 ml) and added to the reaction mixture which was heated to 50° C. for 24 hr. The solution was quenched with aqueous MeCN (50:50, 1 ml) and neutralised. Solvent was removed in a blowdown unit. The crude residue was dissolved in DMF (200 μl), Acetone (200 μl) and water (20 μl) and purified by MDAP (Method D). The solvent was removed in vacuo using the Genevac to give the title compound.

Provenance & Evidence