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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 497040Generated: October 30, 2026

Binap, (A+-)- → N-[5-({2-[(6-amino-5-nitropyridin-2-yl)amino]ethyl}amino)-3-(2,4-dichlorophenyl)pyrazin-2-yl]acetamide

https://huagongshe.com/reaction/497040

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBinap, (A+-)-HCID 634876—
Reactant2,6-Diamino-N2-(2-aminoethyl)-5-nitropyridineHCID 22142380—
ReactantN-acetyl-N-[3-(2,4-dichlorophenyl)-6-bromopyrazin-2-yl]acetamideHCID 22318506—
ReactantSodium t-butoxideHCID 23676156—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductN-[5-({2-[(6-amino-5-nitropyridin-2-yl)amino]ethyl}amino)-3-(2,4-dichlorophenyl)pyrazin-2-yl]acetamideHCID 10162637—

Reaction Conditions

Temperature80 °C

Reaction Steps

A solution of N-acetyl-N-[3-(2,4-dichlorophenyl)-6-bromopyrazin-2-yl]acetamide (57 mg, 0.14 mmol) in DMF (2 ml) were added (2-aminoethyl)(6-amino-5-nitro(2-pyridyl))amine (28 mg, 0.141 mmol), sodium tert-butoxide (20 mg, 0.21 mmol), BINAP (38 mg, 0.06 mmol) and palladium acetate (10 mg, 0.04 mmol). The reaction mixture was stirred overnight at 80° C. The solution was cooled to room temperature, taken in ethyl acetate and water. The layers were separated and the organic layer was washed with water and brine, dried, concentrated and purified to afford the title product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06949547B2
Source datasetuspto-grants-2005_09
ORD IDord-3c44365bc7f848089e18f2fbea2467f6
Source noteuspto-grants-2005_09