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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 255373Generated: October 30, 2026

2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde → 4-(2-{(2S,5R)-5-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-2-yl}ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

https://huagongshe.com/reaction/255373

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 21873668—
Reactanttert-Butyl (2R,5S)-5-amino-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylateHCID 66774232—
Reactanttert-butyl (2S,5R)-5-amino-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylateHCID 66775001—
Reactant1-tert-butyl 2-ethyl (2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1,2-dicarboxylateHCID 69185078—
Reactant1-tert-butyl 2-ethyl (2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1,2-dicarboxylateHCID 86642662—
Product4-(2-{(2S,5R)-5-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-2-yl}ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrileHCID 66774824—

Reaction Steps

The product was obtained following the procedure described for Example 105, except, the enantiomer of Intermediate 183, tert-butyl (2S,5R)-5-amino-2-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidine-1-carboxylate (prepared by the exact route as Intermediate 183, but starting from 1-tert-butyl 2-ethyl (2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1,2-dicarboxylate, the enantiomer of Intermediate 191) was reacted with 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde to yield the named compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07875715B2
Source datasetuspto-grants-2011_01
ORD IDord-e0e3ac3eaf3f44cab19d4568b58ae558
Source noteuspto-grants-2011_01