Dichloromethane → HCID 73197256, Verbindung

HRID 2297550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2297550
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:23])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20](=O)[CH3:21])[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:24])[C:5]([C:25]([OH:27])=[O:26])=[CH:4]1)[CH3:2].Cl.[NH2:29][OH:30].C(=O)(O)[O-].[Na+].C(Cl)Cl>CO.O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:23])=[C:10]([N:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20](=[N:29][OH:30])[CH3:21])[CH2:17][CH2:18]3)[CH:11]=2)[C:6](=[O:24])[C:5]([C:25]([OH:27])=[O:26])=[CH:4]1)[CH3:2]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 136887983-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(4-(2-oxopropyl)-1-piperazinyl)-

Produkt 1

HCID 73197256HCID 73197256, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of the 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)-1-piperazinyl]-quinoline-3-carboxylic acid [H. Kondo et. al., J. Med. Chem., 29, 2020 (1986)] (0.38 g, 1 mmol) in absolute methanol (20 ml) was added a solution of hydroxylamine hydrochloride (0.14 g, 2 mmol) and sodium bicarbonate (0.17 g, 2 mmol) in water (2 ml). The mixture was stirred for 20 hr at room temperature, then CH2Cl2 (50 ml) was added, and the layers were separated. The organic phase was washed successively with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to give a solid which was purified by flash column chromatography (silica gel, with CH2Cl2/methanol (10:1) as the eluant) and crystillization from CH2Cl2/methanol 5:1 to give 1-ethyl-6-fluoro-7-[4-(2-hydroxyiminopropyl)-1-piperazinyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid as an off-white amorphous solid (0.28 g, 72%). Mp: 218° C. (dec). 1H NMR (DMSO-d6) δ1.41 (t, 3H, J=7.2), 1.81 (s, 3H), 2.54 (m, 4H), 3.03 (s, 2H2), 3.33 (m, 4H), 4.57 (q, 2H, J=7.2), 7.17 (d, H, J=7.2), 7.90 (d, 1H, J=13.6), 8.92 (s, 1H), 10,61 (s, 1H), 15.27 (br s, 1H). Anal. Calcd. for C19H23FN4O4•0.5 H2O: C, 57.14; H. 6.06; N, 14.03. Found: C, 57.43; H, 5.87; N, 13.83.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic phase was washed successively with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a solid which
  7. customwas purified by flash column chromatography (silica gel

Quellen und Nachweise

ORD-Eintrag
ord-99d944ade6464483945c06a61fde8aa3
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06492373B2

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