Triethylamine → HCID 23284723, compound

HRID 369313Notes

Reaction equation

HRID 369313 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].Cl.[CH2:28]([O:30][C:31](=[O:34])[CH2:32][NH2:33])[CH3:29].C(N(CC)CC)C>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:33][CH2:32][C:31]([O:30][CH2:28][CH3:29])=[O:34])[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 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 154349011-(6-Amino-3,5-difluoro-2-pyridinyl)-8-chloro-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 23284723HCID 23284723, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(6-Amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (200 mg), glycine ethyl ester hydrochloride (135 mg) and triethylamine (450 mg) were added to pyridine (1,000 mg), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure. A process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure was conducted 4 times repeatedly. Ethanol (1 ml) and distilled water (1 ml) were added to the resultant residue, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain an about 1:1 mixture (106 mg) of the title compound and 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, which is the raw material, as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationA process of adding ethanol (2 ml) to the residue and then concentrating the mixture under reduced pressure
  3. distillationEthanol (1 ml) and distilled water (1 ml)
  4. additionwere added to the resultant residue, and deposits
  5. filtrationwere collected by filtration
  6. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-8d44616019714916b96bdd811bf8ef91
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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