Pyridine → HCID 23284800, compound

HRID 369290Notes

Reaction equation

HRID 369290 reaction equation
[N:1]1C=CC=C[CH:2]=1.CN.[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1F)[N:16]([C:22]1[CH:27]=[C:26]([NH:28][CH3:29])[C:25]([F:30])=[CH:24][C:23]=1[F:31])[CH:15]=[C:14]([C:32]([OH:34])=[O:33])[C:13]2=[O:35]>C(OCC)C>[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([CH3:21])[C:19]=1[NH:1][CH3:2])[N:16]([C:22]1[CH:27]=[C:26]([NH:28][CH3:29])[C:25]([F:30])=[CH:24][C:23]=1[F:31])[CH:15]=[C:14]([C:32]([OH:34])=[O:33])[C:13]2=[O:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 23284750HCID 23284750, compound

Product 1

HCID 23284800HCID 23284800, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

Pyridine (300 mg) and a 40% aqueous solution (150 mg) of methylamine were added to 6,7-difluoro-1-(2,4-difluoro-5-methylaminophenyl)-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (80 mg), and the mixture was heated and stirred at 40° C. for 3 days. After the reaction mixture was allowed to cool, diethyl ether was added, followed by stirring. A supernatant liquid was removed, and ethanol (1 ml) was added to the residue to disperse solids therein. The solids were collected by filtration and washed with ethanol and dried to obtain the title compound (20 mg) as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool
  3. stirringby stirring
  4. customA supernatant liquid was removed
  5. additionethanol (1 ml) was added to the residue
  6. additionto disperse solids
  7. filtrationThe solids were collected by filtration
  8. washwashed with ethanol
  9. customdried

Sources & evidence

ORD record
ord-68ba3345bbce466a92f655cbcae5fb0c
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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