Pyridine → HCID 67485959, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with (R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (1.53 g, 5.15 mmol), pyridine (1.25 ml, 15.4 mmol), sodium thiocyanate (0.417 g, 5.15 mmol) and acetonitrile (15 mL). The solution was heated to 40° C. for 40 minutes. 5-Bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-amine (1.02 g, 3.43 mmol) was added and the reaction was heated to 70° C. overnight. The reaction was cooled to ambient temperature, partitioned between EtOAc and water, dried over sodium sulfate, filtered and concentrate. The residue was purified over silica gel (10% MeOH/EtOAc) to afford (S)-N-(5-Bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)pyridin-2-yl)-3-(1,4-dioxaspiro[4.5]decane-2-yl)-1,2,4-thiadiazol-5-amine (1.66 g, 3.18 mmol, 92.7% yield) as a yellow solid.

Provenance & Evidence