1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 14839395, compound

HRID 2165674Notes

Reaction equation

HRID 2165674 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].[CH:19]1([CH:22]2[NH:27][CH2:26][CH2:25][NH:24][CH2:23]2)[CH2:21][CH2:20]1>N1C=CC=CC=1>[CH:19]1([CH:22]2[NH:27][CH2:26][CH2:25][N:24]([C:10]3[CH:11]=[C:12]4[C:7]([C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4][N:3]4[CH2:1][CH3:2])=[CH:8][C:9]=3[F:14])[CH2:23]2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 197635402-Cyclopropylpiperazine

Product 1

HCID 14839395HCID 14839395, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.265 g of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.86 g of 3-cyclopropylpiperazine and 15 ml of pyridine was heated at 100° C. in a pressure bottle for 3 hours, then cooled and evaporated. The residue was purified by silica gel flash chromatography, eluting with chloroform:methanol:water:triethylamine (9:0.5:0.02:0.02), giving 180 mg of the desired product, mp 250° C. (dec.).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was purified by silica gel flash chromatography
  4. washeluting with chloroform:methanol:water:triethylamine (9:0.5:0.02:0.02)

Sources & evidence

ORD record
ord-a62dcd226db34da88cd6f25ae633eccc
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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