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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1593393Generated: October 30, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → (2R,5S)-4-(4-Cyano-3-methoxyphenyl)-2,5-dimethyl-N-(6-trifluoromethyl-3-pyridyl)piperazine-1-carboxamide

https://huagongshe.com/reaction/1593393

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantMethyl [6-(trifluoromethyl)pyridin-3-yl]carbamateHCID 23082060—
Reactant4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-methoxybenzonitrileHCID 68691204—
SolventTolueneHCID 1140—
Product(2R,5S)-4-(4-Cyano-3-methoxyphenyl)-2,5-dimethyl-N-(6-trifluoromethyl-3-pyridyl)piperazine-1-carboxamideHCID 1032064145.7%

Reaction Conditions

Temperature100 °C

Reaction Steps

Into 5 ml of toluene were dissolved 500 mg of methyl 6-(trifluoromethyl)pyridin-3-ylcarbamate and 557 mg of 4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-methoxybenzonitrile, and then 0.03 ml of DBU was added thereto, followed by heating to 100° C. and 8 hours of stirring. The reaction solution was concentrated and the residue was subjected to silica gel column chromatography to obtain 450 mg of the title compound from an eluate using chloroform-methanol (96:4, v/v).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07297698B2
Source datasetuspto-grants-2007_11
ORD IDord-a8e5c6e648354bd48430ca0b182a183a
Source noteuspto-grants-2007_11