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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1694146Generated: November 1, 2026

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

https://huagongshe.com/reaction/1694146

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 numberUS08158657B2
Source datasetuspto-grants-2012_04
ORD IDord-971b2d235df74437bbb10fb713437230
Source noteuspto-grants-2012_04