1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-aminopyridine-2-carboxamide

HRID 714905Notes

Reaction equation

HRID 714905 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[Cl-].[NH4+].C([N:15]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH2:15])=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 41797265-Aminopyridine-2-carboxylic acid

Product 1

HCID 104643925-aminopyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-aminopyridine-2-carboxylic acid (2.0 g) in N,N-dimethylformamide (50 mL) were added ammonium chloride (3.9 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (5.1 mL) and 1-hydroxybenzotriazole (4.4 g), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (260 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-aab3fd36a97149bc8115f1062511f824
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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