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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2035545Generated: October 26, 2026

4-Aminopyridine → 4-Benzylamino-6-(pyridin-4-ylamino) pyridine-3-carboxyamide

https://huagongshe.com/reaction/2035545

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-AminopyridineHCID 1727—
ReactantPotassium CarbonateHCID 11430—
ReactantBinap, (A+-)-HCID 634876—
Reactant(1-Benzylpyrrolidin-2-yl)methanamineHCID 9855700—
Reactant4-Benzylamino-6-chloropyridine-3-carboxyamideHCID 131730930—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
Product4-Benzylamino-6-(pyridin-4-ylamino) pyridine-3-carboxyamideHCID 13173100916%

Reaction Conditions

Temperature100 °C

Reaction Steps

25 mg of 4-benzylamino-6-chloropyridine-3-carboxyamide (the compound of Example 1) was dissolved in 0.5 ml of toluene, to which 13.5 mg of 4-aminopyridine, 2 mg of palladium (II) acetate, 248 mg of potassium carbonate and 11 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl were added, and stirred at 100° C. for 28 hours. After cooling, the insoluble substances were filtered off, the filtered product was washed with toluene, combined with the filtrate, and the solvent was evaporated. The residue obtained was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 4.8 mg (yield 16%) of the title compound as a slight yellow crystalline powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08575153B2
Source datasetuspto-grants-2013_11
ORD IDord-31071e56a1de4f03a46aed7b444fcafc
Source noteuspto-grants-2013_11