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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1644502Generated: October 31, 2026

Methanol → 6-Chloro-4-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-1,2,4-benzotriazin-3(4H)-one 1-oxide

https://huagongshe.com/reaction/1644502

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
Reactant2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 21873668—
ReactantSodiumacetoxyborohydrideHCID 23670382—
Reactant4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-chloro-1,2,4-benzotriazin-3(4H)-one 1-oxideHCID 86642660—
SolventAcetic AcidHCID 176—
SolventDichloromethaneHCID 6344—
Product6-Chloro-4-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-1,2,4-benzotriazin-3(4H)-one 1-oxideHCID 25031067—

Reaction Steps

4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-chloro-1,2,4-benzotriazin-3(4H)-one 1-oxide (Intermediate 205, (0.25 g) was reacted with 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (WO 2004/058144) (0.14 g) and sodium acetoxyborohydride (0.34 g) as described for Example 107. Chromatography on silica gel with 0-20% methanol in dichloromethane gave 60 mg of the title compound as acetic acid salt (0.37 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08124602B2
Source datasetuspto-grants-2012_02
ORD IDord-f0f95110c2b745e48e418df4fca49d2d
Source noteuspto-grants-2012_02