6-Aminonicotinic acid → HCID 54352395, compound

HRID 2295019Notes

Reaction equation

HRID 2295019 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:33]([C:35](=[CH:40][CH3:41])[CH:36]=[CH:37][CH2:38][NH2:39])[CH3:34]>CN(C)C=O.CN(C)C1C=CN=CC=1.C(=O)([O-])O.[Na+]>[CH2:40]([C:35](=[CH:33][CH3:34])[CH:36]=[CH:37][CH2:38][NH:39][C:8]([C:5]1[CH:6]=[N:7][C:2]([NH2:1])=[CH:3][CH:4]=1)=[O:10])[CH3:41]

Participants

8

Reactant 4

HCID 184966-Aminonicotinic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 539452134-Ethyl-2,4-hexadien-1-ylamine

Product 1

HCID 54352395HCID 54352395, compoundYield 75.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 6-aminopyridine-3-carboxylic acid (4.24 g), N-hydroxybenzotriazole (5.13 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.44 g) in N,N-dimethylformamide (100 ml) was stirred at 0° C. for 10 minutes. A solution of 4-ethyl-2,4-hexadien-1-ylamine (4.24 g) in N,N-dimethylformamide (50 ml) was added dropwise to the mixture over a period of 10 minutes and 4-dimethylaminopyridine (4.0 g) was added to the mixture. The mixture was stirred at 0° C. for 2 hours and then at room temperature overnight. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (4% methanol-chloroform) to give N-(4-ethyl-2,4-hexadien-1-yl)-6-amino-3-pyridinecarboxamide (5.7 g).

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 hours
  2. customat room temperature
  3. customovernight
  4. extractionextracted three times with ethyl acetate
  5. washThe extract was washed with aqueous sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed on silica gel (4% methanol-chloroform)

Sources & evidence

ORD record
ord-1679992afbea49c79be0a95b68f5c1d2
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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