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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 84908Generated: October 25, 2026

Ethyl Acetate → (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide

https://huagongshe.com/reaction/84908

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantDiisopropylethylamineHCID 81531—
Reactant2,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 2733849—
Reactant(2R)-2-aminobutanamide hydrochlorideHCID 16218339—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product(R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamideHCID 8666616098.2%

Reaction Steps

To the mixture of (R)-(−)-2-aminobutanamide hydrochloride (1.00 g, 7.2 mmol) and 2,6-dichloro-5-fluoro-3-pyridinecarbonitrile (0.92 g, 4.8 mmol) in 40 mL NMP added DIEA (2.5 mL, 14.4 mmol). The mixture was then sent to 100° C. for stirring for 1 h. The mixture was cooled to RT, and to it was poured 300 mL EtOAc. The mixture was washed with brine four times. The organic phase was dried, concentrated and purified using silica flash column (70% EtOAc-30% DCM) to isolate (R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamide (1.21 g, 98% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846928B2
Source datasetuspto-grants-2014_09
ORD IDord-ebeeb81edffd47e99c139fc55dd2bd37
Source noteuspto-grants-2014_09