Pyridine → HCID 23284758, compound

HRID 369328Notes

Reaction equation

HRID 369328 reaction equation
[N:1]1C=CC=C[CH:2]=1.CN.[NH2:9][C:10]1[C:11]([F:35])=[CH:12][C:13]([F:34])=[C:14]([N:16]2[C:25]3[C:20](=[C:21]([OH:29])[C:22]([F:28])=[C:23](F)[C:24]=3[CH3:26])[C:19](=[O:30])[C:18]([C:31]([OH:33])=[O:32])=[CH:17]2)[CH:15]=1>C(O)(=O)C.C(O)C>[NH2:9][C:10]1[C:11]([F:35])=[CH:12][C:13]([F:34])=[C:14]([N:16]2[C:25]3[C:20](=[C:21]([OH:29])[C:22]([F:28])=[C:23]([NH:1][CH3:2])[C:24]=3[CH3:26])[C:19](=[O:30])[C:18]([C:31]([OH:33])=[O:32])=[CH:17]2)[CH:15]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6329MethylamineHCID 23284698HCID 23284698, compound

Product 1

HCID 23284758HCID 23284758, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

Pyridine (300 mg) and a 40% aqueous solution (300 mg) of methylamine were added to 1-(5-amino-2,4-difluorophenyl)-6,7-difluoro-5-hydroxy-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (100 mg), and the mixture was stirred at 30° C. for 2 days. Acetic acid (1 drop) and ethanol (1 ml) were added to the reaction mixture, and the solvent was distilled off. Methanol was added to the residue, and solids were collected by filtration to obtain the title compound (33 mg) as a brown powder.

Workup

  1. distillationthe solvent was distilled off
  2. additionMethanol was added to the residue, and solids
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-402a4f0415ec48a398db1da2eba8d09c
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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