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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2200467Generated: October 27, 2026

6-Aminoquinoline → (R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-3-phenylpropanamide

https://huagongshe.com/reaction/2200467

Reaction equation

Participants

RoleNameHCIDCharge
Reactant6-AminoquinolineHCID 11373—
ReactantPotassium CarbonateHCID 11430—
ReactantBinap, (A+-)-HCID 634876—
Reactant(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-phenylpropanamideHCID 86685588—
Catalystpalladium(II) acetateHCID 167845—
Solvent1,4-DioxaneHCID 31275—
Product(R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-3-phenylpropanamideHCID 8668558912.1%

Reaction Steps

A mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-phenylpropanamide (128 mg, 0.424 mmol), 6-aminoquinoline (80 mg, 0.555 mmol), K2CO3 (100 mg, 0.724 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (3 mL) was degassed with Ar, then was stirred at 110 C for 20 h. The mixture was concentrated in vacuo. The residue was purified by HPLC to give (R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-3-phenylpropanamide (21 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09359308B2
Source datasetuspto-grants-2016_06
ORD IDord-4a4147891c224d079cceae47a9786738
Source noteuspto-grants-2016_06