Sodium methanethiolate → HCID 71281396, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[(2-chloropyridin-4-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-2-naphthamide (0.050 g, 0.12 mmol) in 1 mL of DMSO was added sodium thiomethoxide (0.025 g, 0.35 mmol). The mixture was heated in a sealed tube at 100° C. for 18 hours, then cooled to room temperature. Additional sodium thiomethoxide (0.025 g, 0.35 mmol) was added, and the reaction was heated to 120° C. for 3 hours, then recooled to room temperature and diluted with ethyl acetate and water. The aqueous layer was extracted 3× with ethyl acetate and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 1-hydroxy-N-[(1S,2S)-2-hydroxycyclohexyl]-4-{[2-(methylthio)pyridin-4-yl]methyl}-2-naphthamide that gave a mass ion (ES+) of 423.0 for [M+H]+.

Provenance & Evidence