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

HRID 545288Notes

Reaction equation

HRID 545288 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[S:29][CH:30]=[C:31]([CH3:33])[N:32]=1>C(#N)C>[F:1][C:2]1[C:3]([OH:14])=[C:4]([C:11]([NH:27][C:28]2[S:29][CH:30]=[C:31]([CH3:33])[N:32]=2)=[O:13])[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 741432-Amino-4-methylthiazoleHCID 576721225-Fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 576195925-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-N-(4-methyl-2-thiazolyl)-1,2-dihydropyridine-3-carboxamideYield 30.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

200 mg of 5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid was dissolved in 3 ml of acetonitrile, and 162 mg of carbonyldiimidazole was added to this. The mixture was stirred for 1 hour under heat refluxing condition, then, 114 mg of 2-amino-4-methylthiazole was added, and the resulting mixture was further stirred for 1 hour under heat refluxing condition. Thereafter, the reaction mixture was cooled to room temperature. As a result, a crystal was produced. The produced crystal was collected by filtration, to obtain 90 mg of 5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-N-(4-methyl-2-thiazol yl)-1,2-dihydropyridine-3-carboxamide (hereinafter, referred to as present compound 31) represented by the formula:

Workup

  1. temperatureunder heat
  2. temperaturerefluxing condition
  3. stirringthe resulting mixture was further stirred for 1 hour
  4. temperatureunder heat
  5. temperaturerefluxing condition
  6. customAs a result, a crystal was produced
  7. filtrationThe produced crystal was collected by filtration

Sources & evidence

ORD record
ord-ff2824d2808342dc88891b1af6245a09
Source dataset
uspto-grants-2011_05
Patent number
US07935716B2

Reaction notes

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