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

HRID 84908

Reaction equation

HRID 84908 reaction equation
Cl.[NH2:2][C@H:3]([CH2:7][CH3:8])[C:4]([NH2:6])=[O:5].[Cl:9][C:10]1[C:15]([C:16]#[N:17])=[CH:14][C:13]([F:18])=[C:12](Cl)[N:11]=1.CCN(C(C)C)C(C)C.CCOC(C)=O>CN1C(=O)CCC1>[Cl:9][C:10]1[N:11]=[C:12]([NH:2][C@H:3]([CH2:7][CH3:8])[C:4]([NH2:6])=[O:5])[C:13]([F:18])=[CH:14][C:15]=1[C:16]#[N:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 16218339(2R)-2-aminobutanamide hydrochloride

Product 1

HCID 86666160(R)-2-(6-chloro-5-cyano-3-fluoropyridin-2-ylamino)butanamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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).

Workup

  1. customwas then sent to 100° C.
  2. washThe mixture was washed with brine four times
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-ebeeb81edffd47e99c139fc55dd2bd37
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Linked notes

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