Triethylamine → 1-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(3,3,3-trifluoro-2-hydroxypropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

HRID 369309Notes

Reaction equation

HRID 369309 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.[NH2:27][CH2:28][CH:29]([OH:34])[C:30]([F:33])([F:32])[F:31].C(N(CC)CC)C>N1C=CC=CC=1>[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]([NH:27][CH2:28][CH:29]([OH:34])[C:30]([F:33])([F:32])[F:31])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4189653-Amino-1,1,1-trifluoropropan-2-olHCID 108619991-(3-Amino-4,6-difluorophenyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 232847741-(5-Amino-2,4-difluorophenyl)-8-chloro-6-fluoro-7-(3,3,3-trifluoro-2-hydroxypropylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylic AcidYield 79.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

1-(5-Amino-2,4-difluorophenyl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (150 mg), 1-amino-3,3,3-trifluoro-2-propanol (120 mg) and triethylamine (120 mg) were added to pyridine (400 mg), and the mixture was stirred for 20 hours at room temperature and for 6 hours at 60° C. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Concentrated hydrochloric acid (150 mg) was added to the residue, and the mixture was concentrated under reduced pressure. Ethanol (2 ml) was added to the resultant residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (153 mg) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (3 ml) to the residue and then concentrating the mixture under reduced pressure
  3. additionConcentrated hydrochloric acid (150 mg) was added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionEthanol (2 ml) was added to the resultant residue, and deposits
  6. filtrationwere collected by filtration
  7. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-f56d9ac37ede47889fd58883d4e6dc97
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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