Trifluoroacetic acid → 7-[(2-Aminoethyl)amino]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1270078Notes

Reaction equation

HRID 1270078 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.C([NH:29][CH2:30][CH2:31][NH2:32])(OC(C)(C)C)=O.FC(F)(F)C(O)=O>CN(C)C(=O)C.CO>[NH2:29][CH2:30][CH2:31][NH:32][C:11]1[C:12]([O:14][CH3:15])=[C:13]2[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]2[CH:1]2[CH2:3][CH2:2]2)=[CH:9][C:10]=1[F:17]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 187201N-BOC-ethylenediamineHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 184489767-[(2-Aminoethyl)amino]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 58,848.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-cyclopropyl-1,4-dihydro-4-oxo-6,7-difluoro-8-methoxy-3-quinoline carboxylic acid (1.0 g) in N,N-dimethylacetamide (10 ml), N-BOC-ethylenediamine (0.82 mg) was added. The mixture was heated at 120° C. for 12 h. Trifluoracetic acid (20 ml) was added and the reaction mixture was stirred at r.t. for 24 h. The solvent was evaporated under reduced pressure. The crude product was dissolved in water (5 ml) and pH adjusted with 20% NaOH to 7. The precipitate obtained was dispersed in MeOH and filtered to give the title compound (1.01 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe crude product was dissolved in water (5 ml)
  3. customThe precipitate obtained
  4. filtrationfiltered

Sources & evidence

ORD record
ord-28893d5a79ff45318058e6925aea518f
Source dataset
uspto-grants-2007_04
Patent number
US07202221B2

Reaction notes

Loading…