Hydrochloric Acid → HCID 23284806, compound

HRID 369277Notes

Reaction equation

HRID 369277 reaction equation
[NH2:1][C:2]1[N:7]=[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)[C:5]([F:25])=[CH:4][C:3]=1[F:26].[NH2:27][CH:28]([CH3:31])[CH2:29][OH:30].Cl>N1C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:20])=[C:15]([NH:27][CH:28]([CH3:31])[CH2:29][OH:30])[C:16]=3[Cl:18])[C:11](=[O:21])[C:10]([C:22]([OH:24])=[O:23])=[CH:9]2)[C:5]([F:25])=[CH:4][C:3]=1[F:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 51262-AminopropanolHCID 154349011-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 23284806HCID 23284806, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

1-(6-Amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (300 mg) and 2-amino-1-propanol (400 mg) were added to pyridine (1,200 mg), and the mixture was stirred at 45° C. for 16 hours. Concentrated hydrochloric acid (600 mg) was added to the reaction mixture, and the resultant mixture was concentrated under reduced pressure. Ethanol (2 ml) was added to the residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (168 mg) as a colorless powder.

Workup

  1. concentrationthe resultant mixture was concentrated under reduced pressure
  2. additionEthanol (2 ml) was added to the residue, and deposits
  3. filtrationwere collected by filtration
  4. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-ef60f438b238445ab4759b1439baf0e9
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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