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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1183260Generated: October 26, 2026

Tetrahydrofuran → 1-{4'-[4-(2-Benzyl-cyclohexylamino)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

https://huagongshe.com/reaction/1183260

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
Reactant2-Benzylcyclohexan-1-oneHCID 98945—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant1-[4'-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl esterHCID 66577195—
SolventTolueneHCID 1140—
Product1-{4'-[4-(2-Benzyl-cyclohexylamino)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl esterHCID 66577705—

Reaction Conditions

Temperature110 °C

Reaction Steps

1-[4′-(4-Amino-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.200 g, 0.55 mmol) and 2-benzylcyclohexanone (0.156 g, 0.83 mmol) were combined in toluene and stirred at 110° C. for 1 hour. After cooling to room temperature, THF was added, followed by sodium cyanoborohydride (0.086 g, 1.37 mmol), and the reaction was stirred at room temperature for 2 hours. The mixture was adsorbed onto silica gel and purified by silica gel chromatography to give the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08664220B2
Source datasetuspto-grants-2014_03
ORD IDord-51138e95e9f94a4fbb24dbba1eaf37b4
Source noteuspto-grants-2014_03