Ethylenediamine → 7-(2-Aminoethyl)amino-1-(5-amino-2,4-difluorophenyl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 369226Notes

Reaction equation

HRID 369226 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[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1.[CH2:27]([NH2:30])[CH2:28][NH2:29].C(N(CC)CC)C>C(#N)C>[NH2:29][CH2:28][CH2:27][NH:30][C:15]1[C:16]([Cl:18])=[C:17]2[C:12]([C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9][N:8]2[C:6]2[CH:7]=[C:2]([NH2:1])[C:3]([F:26])=[CH:4][C:5]=2[F:25])=[CH:13][C:14]=1[F:20]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 8471TriethylamineHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 232848167-(2-Aminoethyl)amino-1-(5-amino-2,4-difluorophenyl)-8-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (100 mg), ethylenediamine (16 mg) and triethylamine (70 mg) were added to acetonitrile (5 ml), and the mixture was heated under reflux for 2 hours. After the reaction mixture was allowed to cool, deposits were collected by filtration. The deposits were washed successively with ethanol and diethyl ether to obtain the title compound (72 mg) as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. filtrationdeposits were collected by filtration
  5. washThe deposits were washed successively with ethanol and diethyl ether

Sources & evidence

ORD record
ord-8c051533994245df9eca183ed04e9055
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

Loading…