1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloro-N-methoxy-N-methylnicotinamide

HRID 572171Notes

Reaction equation

HRID 572171 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:12][NH:13][O:14][CH3:15].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(=O)([O-])O.[Na+].C(N(CC)CC)C>[Cl:1][C:2]1[C:7]([C:8]([N:13]([O:14][CH3:15])[CH3:12])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 762582-Chloronicotinic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 102360762-Chloro-N-methoxy-N-methylnicotinamideYield 63.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Chloropyridine-3-carboxylic acid (13 g), N,O-dimethylhydroxylamine hydrochloride (8.85 g), HOBt (5.57 g), EDCI (15.37 g) and triethylamine (34.5 ml) were dissolved in DMF (150 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) to give the title compound (10.5 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-826f12a127f94e3286c682ff320c6886
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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