Picolinic acid → HCID 54328936, compound

HRID 1357196Notes

Reaction equation

HRID 1357196 reaction equation
CCN=C=NCCCN(C)C.[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[C:13]1[C:21]1[O:26][C:25](=[O:27])[C:24]([CH3:28])=[C:23](O)[C:22]=1[CH3:30].N1C=CC=CC=1[C:37]([OH:39])=[O:38].[CH:40]1[CH:41]=[CH:42]C2N(O)N=[N:46][C:44]=2[CH:45]=1>CN(C=O)C>[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[C:13]1[C:21]1[O:26][C:25](=[O:27])[C:24]([CH3:28])=[C:23]([C:37]([O:39][C:44]2[CH:45]=[CH:40][CH:41]=[CH:42][N:46]=2)=[O:38])[C:22]=1[CH3:30]

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 54712960HCID 54712960, compound

Product 1

HCID 54328936HCID 54328936, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC (43 mg) was added to a solution of 6-(benzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one (40 mg), picolinic acid (23 mg) and HOBt (21 mg) in DMF (3 ml), and the mixture was stirred at room temperature for 21.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1→3/2) to obtain 6-(benzofuran-2-yl)-3,5-dimethyl-4-(2-pyridylcarboxy)-2H-pyran-2-one.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1→3/2)

Sources & evidence

ORD record
ord-c13bb5720f36421ca4ca7b35a10147ca
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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