Pyridine → HCID 484064, compound

HRID 369319Notes

Reaction equation

HRID 369319 reaction equation
[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15](F)[C:16]=3[CH3:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31].CN1CCCC1.N1C=CC=CC=1>CN(C)C=O>[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([F:25])=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:27][CH2:28][CH2:29][CH2:30][OH:31])[C:16]=3[CH3:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 84541-MethylpyrrolidineHCID 90863-Amino-1-propanolHCID 11132289HCID 11132289, compound

Product 1

HCID 484064HCID 484064, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-8-methyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (500 mg), 3-amino-1-propanol (400 mg) and N-methylpyrrolidine (170 mg) were added to pyridine (1,500 mg), and the mixture was stirred at 70° C. for 15 hours. Since the raw material were not dissolved, N,N-dimethylformamide (1 ml) was added to the mixture, followed by stirring at 70° C. for 43 hours. The reaction mixture was concentrated under reduced pressure. A process of adding distilled water (1 ml) to the residue and then concentrating the mixture under reduced pressure was conducted 3 times repeatedly. Another process of adding toluene (1.5 ml) to the resultant residue and then concentrating the mixture under reduced pressure was conducted 3 times repeatedly. A further process of adding ethanol (1.5 ml) to the resultant residue and then concentrating the mixture under reduced pressure was conducted 3 times repeatedly. Ethanol (1 ml) was added to the resultant residue, and the mixture was heated under reflux for 5 minutes and allowed to cool. Deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (155 mg) as a colorless powder.

Workup

  1. stirringby stirring at 70° C. for 43 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionA process of adding
  4. distillationdistilled water (1 ml) to the residue
  5. concentrationconcentrating the mixture under reduced pressure
  6. concentrationAnother process of adding toluene (1.5 ml) to the resultant residue and then concentrating the mixture under reduced pressure
  7. concentrationA further process of adding ethanol (1.5 ml) to the resultant residue and then concentrating the mixture under reduced pressure
  8. additionEthanol (1 ml) was added to the resultant residue
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 5 minutes
  11. temperatureto cool
  12. filtrationDeposits were collected by filtration
  13. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-002f5013a0dc431087a96dbe163f60d1
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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