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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1694086Generated: October 30, 2026

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

https://huagongshe.com/reaction/1694086

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant3-Ethynylpyridine-2,6-diamineHCID 55281676—
Reactant(4-Cyclohexyloxy-phenyl)-acetohydroximoyl chlorideHCID 72262879—
SolventTetrahydrofuranHCID 8028—
Product3-(3-(4-Cyclohexyloxy-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamineHCID 5925543363.8%

Reaction Steps

To a tetrahydrofuran (3 mL) solution of (4-cyclohexyloxy-phenyl)-acetohydroximoyl chloride (150 mg, 0.56 mmol) described in Manufacturing Example 79-1-4 and 3-ethynyl-pyridine-2,6-diamine (47.6 mg, 0.357 mmol) described in Manufacturing Example 13-1-3 was added triethylamine (195 μL, 1.4 mmol). This reaction mixture was stirred for 4 hours at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1˜ethyl acetate) to obtain the title compound (83 mg, 41%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158657B2
Source datasetuspto-grants-2012_04
ORD IDord-c179b112c7de4610828fb84e5ce121ee
Source noteuspto-grants-2012_04