1,1'-Carbonyldiimidazole → 1,6-dimethyl-5-fluoro-4-hydroxy-2-oxo-N-(6-cyano-3-pyridyl)-1,2-dihydropyridine-3-carboxamide

HRID 549201Notes

Reaction equation

HRID 549201 reaction equation
[F:1][C:2]1[C:3]([OH:14])=[C:4]([C:11]([OH:13])=O)[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[CH3:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]#[N:35])=[N:32][CH:33]=1>C(#N)C>[CH3:9][N:6]1[C:7]([CH3:8])=[C:2]([F:1])[C:3]([OH:14])=[C:4]([C:11]([NH:27][C:28]2[CH:33]=[N:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=2)=[O:13])[C:5]1=[O:10]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 38713955-Aminopyridine-2-carbonitrileHCID 576721225-Fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 576723371,6-dimethyl-5-fluoro-4-hydroxy-2-oxo-N-(6-cyano-3-pyridyl)-1,2-dihydropyridine-3-carboxamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

500 mg of 5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid was dissolved in 5 ml of acetonitrile, and 403 mg of carbonyldiimidazole was added thereto. The mixture was stirred for 1 hour under heat refluxing condition, 297 mg of 5-amino-2-cyanopyridine was added, and the mixture was further stirred for 1 hour under heat refluxing condition. The reaction mixture was cooled to room temperature, and the resulting crystals were collected by filtration to obtain 460 mg of 1,6-dimethyl-5-fluoro-4-hydroxy-2-oxo-N-(6-cyano-3-pyridyl)-1,2-dihydropyridine-3-carboxamide (hereinafter, referred to as present compound 12) represented by the formula:

Workup

  1. temperatureunder heat
  2. additionwas added
  3. stirringthe mixture was further stirred for 1 hour
  4. temperatureunder heat
  5. temperaturerefluxing condition
  6. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-bbd7abf57ebf4e8cad22a107ef77922f
Source dataset
uspto-grants-2011_05
Patent number
US07943638B2

Reaction notes

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