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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1891906Generated: October 31, 2026

Tetrahydrofuran → 5-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-6-methyl-pyridin-2-ylamine

https://huagongshe.com/reaction/1891906

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriethylamineHCID 8471—
Reactant5-Ethynyl-6-methylpyridin-2-amineHCID 55285938—
Reactant4-Benzyloxy-phenyl-acetohydroximoyl chlorideHCID 72262873—
SolventWaterHCID 962—
Product5-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-6-methyl-pyridin-2-ylamineHCID 5925528458.9%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a mixture of 4-benzyloxy-phenyl-acetohydroximoyl chloride (59 mg, 0.21 mmol) described in Manufacturing Example 1-1-3 and tetrahydrofuran (1 mL) were added 5-ethynyl-6-methyl-pyridin-2-ylamine (22 mg, 0.16 mmol) described in Manufacturing Example 187-1-2 and triethylamine (46 μL, 0.33 mmol), which was stirred for 2 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 thus obtained was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:2) to obtain the title compound (35 mg, 57%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08507530B2
Source datasetuspto-grants-2013_08
ORD IDord-6b852b7b530f45d69547211228f3383a
Source noteuspto-grants-2013_08