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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2035969Generated: October 30, 2026

Triethylamine → (9S)-9-[4-(3-chlorophenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

https://huagongshe.com/reaction/2035969

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant(3-Chlorophenyl)boronic acidHCID 2734323—
Reactant4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenolHCID 66748496—
CatalystHCID 178476681HCID 178476681—
SolventDimethylformamideHCID 6228—
Product(9S)-9-[4-(3-chlorophenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideHCID 6674904524.4%

Reaction Steps

A mixture of (3-chlorophenyl)boronic acid (167 mg), 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (100 mg), diacetoxycopper (130 mg), triethylamine (0.248 mL), and powdered 4A MS (1.50 g) in DMF (10 mL) was stirred at room temperature overnight. The mixture was added with NH silica gel, concentrated in vacuo, and purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) to give the title compound (34.0 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08575154B2
Source datasetuspto-grants-2013_11
ORD IDord-c4f2aa723034499fbfe54b62beafaebd
Source noteuspto-grants-2013_11