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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1891897Generated: October 26, 2026

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

https://huagongshe.com/reaction/1891897

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriethylamineHCID 8471—
Reactant5-Ethynylpyridin-2-amineHCID 21954827—
Reactant(2-Benzyloxy-pyridin-5-yl)acetohydroximoyl chlorideHCID 72262842—
SolventWaterHCID 962—
Product5-(3-(6-Benzyloxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamineHCID 5925516612.9%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a tetrahydrofuran (7.00 mL) solution of (2-benzyloxy-pyridin-5-yl)-acetohydroximoyl chloride (191 mg, 0.690 mmol) described in Manufacturing Example 12-1-5 and 5-ethynyl-pyridin-2-ylamine (40.0 mg, 0.339 mmol) described in Manufacturing Example 28-1-3 was added triethylamine (142 μL, 1.02 mmol) under nitrogen atmosphere at room temperature, which was stirred for 3 hours at 60° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was 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=1:1→2:1) to obtain the title compound (15.7 mg, 12.9%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08507530B2
Source datasetuspto-grants-2013_08
ORD IDord-0e6a4609e3c342398386486092f02080
Source noteuspto-grants-2013_08