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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 78188Generated: October 26, 2026

Tetrahydrofuran → 5-(3-(6-Phenoxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamine

https://huagongshe.com/reaction/78188

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriethylamineHCID 8471—
Reactant5-Ethynylpyridin-2-amineHCID 21954827—
Reactant(2-Phenoxy-pyridin-5-yl)acetohydroximoyl chlorideHCID 72262860—
SolventWaterHCID 962—
Product5-(3-(6-Phenoxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamineHCID 5925523830.2%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a tetrahydrofuran (2 mL) solution of 5-ethynyl-pyridin-2-ylamine (30 mg, 0.25 mmol) described in Manufacturing Example 28-1-3 were added (2-phenoxy-pyridin-5-yl)-acetohydroximoyl chloride (100 mg, 0.381 mmol) described in Manufacturing Example 40-1-4 and triethylamine (70.8 μL, 0.508 mmol), which was stirred for 8 hours at 50° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with 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) to obtain the title compound (26 mg, 30%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08841327B2
Source datasetuspto-grants-2014_09
ORD IDord-fa32d548c8e749ad8364f01b482e1c8b
Source noteuspto-grants-2014_09