Pyridine → HCID 23042974, compound

HRID 2165698Notes

Reaction equation

HRID 2165698 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10](F)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]2[CH2:30][NH:29][CH2:28][CH2:27][NH:26]2)[CH:20]=1.N1C=CC=CC=1>CCOCC>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([N:29]3[CH2:28][CH2:27][NH:26][CH:25]([C:21]4[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=4)[CH2:30]3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 38722892-Pyridin-3-yl-piperazine

Product 1

HCID 23042974HCID 23042974, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 177 mg of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 342 mg of 2-(3-pyridinyl)piperazine and 5 ml of pyridine was heated at 90°-95° C. in a pressure bottle for 5 hours, then cooled at room temperature, then at 0° C. Ether was added to triturate the mixture, then the solid was collected and washed with methanol and ether. This solid was redissolved in a hot mixture of chloroform and methanol, filtered and triturated with ether. The precipitate was collected and dried in vacuo, giving 110 mg of the desired product.

Workup

  1. temperaturewas heated at 90°-95° C. in a pressure bottle for 5 hours
  2. customat 0° C
  3. customto triturate the mixture
  4. customthe solid was collected
  5. washwashed with methanol and ether
  6. dissolutionThis solid was redissolved in a hot mixture of chloroform and methanol
  7. filtrationfiltered
  8. customtriturated with ether
  9. customThe precipitate was collected
  10. customdried in vacuo

Sources & evidence

ORD record
ord-3bd36383cb6047f99b89ebeacdaf4b95
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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