6-Amino-3-chloropyridazine → N-(6-chloro-3-pyridazinyl)-5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 548576Notes

Reaction equation

HRID 548576 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[N:29]=[N:30][C:31]([Cl:34])=[CH:32][CH:33]=1>C(#N)C>[Cl:34][C:31]1[N:30]=[N:29][C:28]([NH:27][C:11]([C:4]2[C:5](=[O:10])[N:6]([CH3:9])[C:7]([CH3:8])=[C:2]([F:1])[C:3]=2[OH:14])=[O:13])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 216436-Amino-3-chloropyridazineHCID 682631,1'-CarbonyldiimidazoleHCID 576721225-Fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 57672125N-(6-chloro-3-pyridazinyl)-5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamideYield 53.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

300 mg of 5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid and 266 mg of carbonyldiimidazole were added to 5 ml of acetonitrile. The mixture was stirred for 1 hour under heat refluxing condition. Thereafter, 212 mg of 3-amino-6-chloropyridazine was added to the mixture, and this was further stirred for 1 hour under heat refluxing condition. The reaction mixture was cooled to room temperature and crystals were produced. The crystals were collected by filtration to obtain 250 mg of N-(6-chloro-3-pyridazinyl)-5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide (present compound 19):

Workup

  1. temperatureunder heat
  2. temperaturerefluxing condition
  3. stirringthis was further stirred for 1 hour
  4. temperatureunder heat
  5. temperaturerefluxing condition
  6. customcrystals were produced
  7. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-334886270023491d97b45b1124c16fc5
Source dataset
uspto-grants-2011_05
Patent number
US07943614B2

Reaction notes

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