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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1694091Generated: October 30, 2026

Tetrahydrofuran → 3-(3-(4-(3-Fluoro-phenoxy)-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamine

https://huagongshe.com/reaction/1694091

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriethylamineHCID 8471—
Reactant3-Ethynylpyridine-2,6-diamineHCID 55281676—
Reactant(4-(3-Fluoro-phenoxy)-phenyl)acetohydroximoyl chlorideHCID 72262890—
SolventWaterHCID 962—
Product3-(3-(4-(3-Fluoro-phenoxy)-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamineHCID 5925546234.2%

Reaction Steps

To a tetrahydrofuran (5.00 mL) solution of (4-(3-fluoro-phenoxy)-phenyl)acetohydroximoyl chloride (210 mg, 0.622 mmol) described in Manufacturing Example 81-1-2 and 3-ethynyl-pyridine-2,6-diamine (30.0 mg, 0.225 mmol) described in Manufacturing Example 13-1-3 was added triethylamine (94.1 μL, 0.675 mmol) at room temperature, which was stirred for 30 minutes at room temperature. Water was added to the reaction solution at room temperature, which was extracted with ethyl acetate. The organic layer washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=2:1) to obtain the title compound (29.0 mg, 34.2%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08158657B2
Source datasetuspto-grants-2012_04
ORD IDord-3169d49674e74ca58f402f7942f20eab
Source noteuspto-grants-2012_04