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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1891842Generated: November 1, 2026

Tetrahydrofuran → 3-(3-(6-(2-Fluorophenoxy)-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2,6-diamine

https://huagongshe.com/reaction/1891842

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriethylamineHCID 8471—
Reactant3-Ethynylpyridine-2,6-diamineHCID 55281676—
Reactant(6-(2-Fluoro-phenoxy)-pyridin-3-yl)-acetohydroximoyl chlorideHCID 72262887—
SolventWaterHCID 962—
Product3-(3-(6-(2-Fluorophenoxy)-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2,6-diamineHCID 5925521445.9%

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 3-ethynyl-pyridin-2,6-diamine (10 mg, 0.075 mmol) described in Manufacturing Example 13-1-3 and triethylamine (21 μL, 0.15 mmol), which was stirred for 5 hours at room temperature. Water was added to the reaction mixture at the same temperature, which 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 alone) to obtain the title compound (13 mg, 45%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08507530B2
Source datasetuspto-grants-2013_08
ORD IDord-dc4f6b4069fd49389d9697042299b479
Source noteuspto-grants-2013_08