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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2066863Generated: October 25, 2026

Ethyl Acetate → 4-(3'-Fluoro-5'-formyl-2,3,5,6-tetrahydro-[1,2]bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl ester

https://huagongshe.com/reaction/2066863

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantDiisopropylethylamineHCID 81531—
Reactant6-Chloro-5-fluoropyridine-3-carbaldehydeHCID 21698194—
ReactantIsopropyl 4-(Piperidin-4-ylideneaminooxy)piperidine-1-carboxylateHCID 57461147—
SolventDimethyl SulfoxideHCID 679—
Product4-(3'-Fluoro-5'-formyl-2,3,5,6-tetrahydro-[1,2]bipyridinyl-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl esterHCID 86655011—

Reaction Conditions

Temperature60 °C

Reaction Steps

2d (0.45 g, 1.6 mmol), 6-chloro-5-fluoro-pyridine-3-carbaldehyde 53a (0.6 g, 3.76 mmol) and diisopropylethylamine (0.75 mL, 4.5 mmol) were combined in 5 mL of DMSO and heated at 60° C. for 18 h. The mixture was poured into ethyl acetate (30 mL), washed with water (2×20 mL) and brine (2×20 mL) and concentrated to give the crude 53b.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08293729B2
Source datasetuspto-grants-2012_10
ORD IDord-ba959599cd8c4c419297824a9edb996d
Source noteuspto-grants-2012_10