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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1772894Generated: November 3, 2026

Pyridine → tert-Butyl [5-(1,1-dioxido-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazin-2-yl)-2-methoxypyridin-3-yl]methylcarbamate

https://huagongshe.com/reaction/1772894

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
ReactantTriethylamineHCID 8471—
Reactant2-Nitrobenzenesulfonyl chlorideHCID 15540—
Reactant1,1'-CarbonyldiimidazoleHCID 68263—
ReactantTert-butyl(5-amino-2-methoxypyridin-3-yl)methylcarbamateHCID 131734691—
CatalystPalladiumHCID 23938—
SolventDimethylformamideHCID 6228—
Solvent1,4-DioxaneHCID 31275—
SolventWater ethanolHCID 19096565—
Producttert-Butyl [5-(1,1-dioxido-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazin-2-yl)-2-methoxypyridin-3-yl]methylcarbamateHCID 13173469396.8%

Reaction Steps

The title compound (2.12 g, 4.84 mmol) was prepared in three steps from 2-nitrobenzenesulfonyl chloride (1.11 g, 5.0 mmol), tert-butyl(5-amino-2-methoxypyridin-3-yl)methylcarbamate (IntA34) (1.39 g, 5.5 mmol) and pyridine (1.21 mL, 15.0 mmol) in 1,4-dioxane (20 mL); followed by followed by 10% Pd/C (212 mg) in water/EtOH (1:1, 100 mL); followed by 1,1′-carbonyldiimidazole (1.14 g, 7.02 mmol) and triethylamine (0.49 mL, 3.51 mmol) in DMF (8 mL) using the methods of (IntA1), step 1 and (IntA14), steps 2 and 3.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09249160B2
Source datasetuspto-grants-2016_02
ORD IDord-459c0a9b210f48d89189f209fbd693ed
Source noteuspto-grants-2016_02