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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 78094Generated: October 29, 2026

Tetrahydrofuran → 3-(3-(4-(5-Methyl-furan-2-ylmethyl)-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamine

https://huagongshe.com/reaction/78094

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriethylamineHCID 8471—
Reactant3-Ethynylpyridine-2,6-diamineHCID 55281676—
Reactant(4-(5-Methyl-furan-2-ylmethyl)-phenyl)acetohydroximoyl chlorideHCID 72262866—
SolventWaterHCID 962—
Product3-(3-(4-(5-Methyl-furan-2-ylmethyl)-benzyl)-isoxazol-5-yl)-pyridin-2,6-diamineHCID 5925534476%

Reaction Conditions

Temperature40 °C

Reaction Steps

To a mixture of (4-(5-methyl-furan-2-ylmethyl)-phenyl)-acetohydroximoyl chloride (11 mg, 0.043 mmol) described in Manufacturing Example 46-1-6 and tetrahydrofuran (1 mL) were added 3-ethynyl-pyridin-2,6-diamine (4.5 mg, 0.034 mmol) described in Manufacturing Example 13-1-3 and triethylamine (9.4 μL, 0.068 mmol), which was stirred for 3 hours at 40° C. Water was added thereto 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: heptane=3:2) to obtain the title compound (9.2 mg, 76%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08841327B2
Source datasetuspto-grants-2014_09
ORD IDord-86472e1dbb3d4e81b93ccff31d956d4e
Source noteuspto-grants-2014_09