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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1951545Generated: November 2, 2026

(2Z)-3-Amino-2-butenenitrile → 4-(4-Cyano-2-methoxyphenyl)-6-ethyl-2-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrile

https://huagongshe.com/reaction/1951545

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2Z)-3-Amino-2-butenenitrileHCID 5325263—
Reactant4-Formyl-3-methoxybenzonitrileHCID 16659251—
Reactant1-(4-Methyl-1,3-thiazol-2-yl)butan-2-oneHCID 59492337—
SolventIsopropanolHCID 3776—
Product4-(4-Cyano-2-methoxyphenyl)-6-ethyl-2-methyl-5-(4-methyl-1,3-thiazol-2-yl)-1,4-dihydropyridine-3-carbonitrileHCID 135844961—

Reaction Steps

100 mg (0.620 mmol) of the compound from example 3A, 100 mg (0.310 mmol, 50% purity) of the compound from example 5A and 51 mg (0.620 mmol) of 3-aminocrotononitrile are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, and the crude product is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 78 mg (66% of theory) of the title compound are obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08404723B2
Source datasetuspto-grants-2013_03
ORD IDord-34dfbf5742e74ed1a39e39d638163559
Source noteuspto-grants-2013_03