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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 78192Generated: October 26, 2026

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

https://huagongshe.com/reaction/78192

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriethylamineHCID 8471—
Reactant5-Ethynylpyridin-2-amineHCID 21954827—
Reactant(6-(2-Fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chlorideHCID 72262887—
SolventWaterHCID 962—
Product5-(3-(6-(2-Fluoro-phenoxy)-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamineHCID 5925537817%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a mixture of (6-(2-fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chloride (28 mg) described in Manufacturing Example 74-1-4 and tetrahydrofuran (1 mL) were added 5-ethynyl-pyridin-2-ylamine (9.0 mg, 0.076 mmol) described in Manufacturing Example 28-1-3 and triethylamine (21 μL, 0.15 mmol), which was stirred for 5 hours at 50° C. The reaction mixture was allowed to room temperature, water was added at the same temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (4.6 mg, 17%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08841327B2
Source datasetuspto-grants-2014_09
ORD IDord-ee1a8c9adfa64fdbb56f25a5e1d214a5
Source noteuspto-grants-2014_09