4-Aminopyridine → Methyl 3-oxo-3-[(pyridin-4-yl)amino]propanoate

HRID 418596Notes

Reaction equation

HRID 418596 reaction equation
Cl[C:2](=[O:7])[CH2:3][C:4]([O-:6])=[O:5].[N:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1.[CH3:15]CN(CC)CC>C(Cl)Cl>[O:7]=[C:2]([NH:14][C:11]1[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=1)[CH2:3][C:4]([O:6][CH3:15])=[O:5]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 18671482HCID 18671482, compound

Product 1

HCID 58790416Methyl 3-oxo-3-[(pyridin-4-yl)amino]propanoateYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-chloro-3-oxopropanoate (1 mL, 9.32 mmol), pyridin-4-amine (0.88 g, 9.32 mmol), and Et3N (1.3 mL, 9.32 mmol) in DCM (18.6 mL) was stirred for 2 h at room temperature. The mixture was concentrated and the residue was purified by flash chromatography (eluent EtOAc/MeOH, 19/1) to produce methyl 3-oxo-3-(pyridin-4-ylamino)propanoate (507.7 mg). Part of this material (207 mg) was re dissolved in THF (1 mL); treated with LiOH×H2O (90 mg, 2.14 mmol) in H2O (1 mL) for 1 h at room temperature. The THF was removed under reduced pressure and the residue was lyophilized to afford the title compound 33 (containing 1 equivalent LiCl) (243.1 mg, 100% yield) as a white solid, which was used in the next step without further purification. MS (m/z): 181.0 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography (eluent EtOAc/MeOH, 19/1)

Sources & evidence

ORD record
ord-82863403865c43308385a9d480888f6a
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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