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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1630716Generated: October 31, 2026

Hydrochloric Acid → 4-{[(6-Chloro-3,5-dicyano-4-phenylpyridin-2-yl)thio]methyl}-N-methylpyridine-2-carboxamide

https://huagongshe.com/reaction/1630716

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantIsoamyl NitriteHCID 8053—
Reactant4-{[(6-Amino-3,5-dicyano-4-phenylpyridin-2-yl)sulfanyl]methyl}-N-methylpyridine-2-carboxamideHCID 56592008—
CatalystCupric ChlorideHCID 24014—
SolventAcetonitrileHCID 6342—
Product4-{[(6-Chloro-3,5-dicyano-4-phenylpyridin-2-yl)thio]methyl}-N-methylpyridine-2-carboxamideHCID 58297347—

Reaction Conditions

Temperature60 °C

Reaction Steps

1.42 g (3.55 mmol) of the compound from Example 24A are initially charged in 30 ml of acetonitrile, 0.96 ml (7.10 mmol) of isopentyl nitrite and 0.95 g (7.10 mmol) of copper(II) chloride are added and the mixture is stirred at 60° C. for 5 hours. Once more, the same amount of copper(II) chloride is added and the mixture is stirred at 60° C. overnight. 7 ml of 1N hydrochloric acid are added, the mixture is extracted three times with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated. The residue is purified by preparative HPLC (with 0.1% TFA added).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08791146B2
Source datasetuspto-grants-2014_07
ORD IDord-24e07d5bd2e144099c557982b0280caa
Source noteuspto-grants-2014_07