Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1809647Generated: October 31, 2026

Pyridine → 1-(4-(5-(5-Bromo-3-hydroxypyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone

https://huagongshe.com/reaction/1809647

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
ReactantSodium thiocyanateHCID 516871—
Reactant5-Bromo-3-(3-methylpyridazin-4-yloxy)pyridin-2-amineHCID 67485345—
Reactant1-acetyl-N-(methylsulfonyloxy)piperidine-4-carbimidoyl chlorideHCID 86641096—
SolventWaterHCID 962—
SolventAcetonitrileHCID 6342—
Product1-(4-(5-(5-Bromo-3-hydroxypyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanoneHCID 6748729951.7%

Reaction Conditions

Temperature40 °C

Reaction Steps

1-Acetyl-N-(methylsulfonyloxy)piperidine-4-carbimidoyl chloride (0.15 g, 0.53 mmol), pyridine (0.13 ml, 1.6 mmol), and sodium thiocyanate (0.043 g, 0.53 mmol) were dissolved in acetonitrile (5 mL). The solution was heated to 40° C. for 40 minutes. 5-Bromo-3-(3-methylpyridazin-4-yloxy)pyridin-2-amine (0.10 g, 0.35 mmol) was added and the reaction was heated at 60° C. overnight. The solution was cooled and charged with water. The solid was filtered and dried to give 1-(4-(5-(5-bromo-3-hydroxypyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidin-1-yl)ethanone (0.072 g, 51%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08362037B2
Source datasetuspto-grants-2013_01
ORD IDord-f4d48ab4fd2e47f8ac1cad398ae99ab8
Source noteuspto-grants-2013_01