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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1891828Generated: October 31, 2026

Triethylamine → 3-(3-(4-Butoxy-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamine

https://huagongshe.com/reaction/1891828

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant3-Ethynylpyridine-2,6-diamineHCID 55281676—
Reactant(4-Butoxy-phenyl)-acetohydroximoyl chlorideHCID 72262872—
SolventTetrahydrofuranHCID 8028—
Product3-(3-(4-Butoxy-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamineHCID 25114605115.7%

Reaction Steps

To a tetrahydrofuran (3 mL) solution of (4-butoxy-phenyl)-acetohydroximoyl chloride (150 mg, 0.621 mmol) described in Manufacturing Example 67-1-4 and 3-ethynyl-pyridin-2,6-diamine (52.8 mg, 0.396 mmol) described in Manufacturing Example 13-1-3 was added triethylamine (216 μL, 1.55 mmol). This mixture was stirred for 4 hours at room temperature. The mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1˜ethyl acetate) to obtain the title compound (155 mg, 74%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08507530B2
Source datasetuspto-grants-2013_08
ORD IDord-945ac8870e6d4d45983372847dfbed1e
Source noteuspto-grants-2013_08