Potassium trimethylsilanolate → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(5-methyl-7,8-dihydroquinolin-2-yl)amino]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-((1R,2S)-2-aminocyclohexylamino)-3-(5-methyl-7,8-dihydroquinolin-2-ylamino)picolinonitrile (19 mg, 0.051 mmol) and potassium trimethylsilanolate (98 mg, 0.76 mmol) in 1,4-dioxane (1 mL) was heated to 100° C. in an oil bath for 3 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was diluted with DMSO, filtered, and purified by reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to yield 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(5-methyl-7,8-dihydroquinolin-2-yl)amino]pyridine-2-carboxamide. MS ESI calc'd. for C22H29N6O [M+H]+ 393. found 393.

Provenance & Evidence