1-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 23042962, compound

HRID 248524Notes

Reaction equation

HRID 248524 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].[C:19]([CH:21]1[NH:26][CH2:25][CH2:24][NH:23][CH2:22]1)#[CH:20]>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:14])=[C:10]([N:23]3[CH2:24][CH2:25][NH:26][CH:21]([C:19]#[CH:20])[CH2:22]3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 8005211-Ethyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 19763589HCID 19763589, compound

Product 1

HCID 23042962HCID 23042962, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.12 g of 1-ethyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.95 g of 3-ethynylpiperazine and 15 ml of pyridine is heated at 100° C. in a pressure bottle for 3 hours, then cooled and evaporated. The residue is purified by silica gel flash chromatography, eluting with chloroform:methanol:water:triethylamine (9:0.5:0.02:0.02), giving 200 mg of the desired product.

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residue is 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-10098270bc8b425ba698e0a39b1ba86b
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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