Acetic Acid → HCID 53724661, Verbindung

HRID 344853

Reaktionsgleichung

Reaktionsgleichung von HRID 344853
Cl[C:2]1[C:3]([F:21])=[CH:4][C:5]2[C:6]([CH:20]=1)=[N:7][C:8]1[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][NH:33][CH2:32][CH2:31][NH:30]2)=[CH:25][CH:24]=1.O.C(O)(=O)C>N1C=CC=CC=1>[F:21][C:3]1[C:2]([N:33]2[CH2:32][CH2:31][NH:30][CH:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)[CH2:34]2)=[CH:20][C:6]2=[N:7][C:8]3[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=3[CH:14]=[C:5]2[CH:4]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 46176232-(4-Fluorophenyl)piperazineHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Produkt 1

HCID 53724661HCID 53724661, VerbindungAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A suspension of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (1.6 g) and (RS)-2-(4-fluorophenyl)piperazine (3.7 g) in pyridine (16 cc) is heated to a temperature in the region of 115° C. for 24 hours. The reaction mixture is concentrated under reduced pressure (20 kPa) at approximately 60° C. The residue is taken up with ethanol (40 cc) and concentrated again under reduced pressure under the above conditions. The solid obtained is taken up with water (10 cc), treated with 10% strength acetic acid (1.75 cc), drained and washed with water (2×10 cc) and ethanol (2×10 cc). After 2 recrystallizations in dimethylformamide (10 cc each time), (RS)-7-fluoro-8-[3-(4-fluorophenyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b ][1,8]naphthyridine-3-carboxylic acid (1.1 g) is obtained in the form of a yellow solid, m.p. 270°-275° C.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at approximately 60° C
  2. concentrationconcentrated again under reduced pressure under the above conditions
  3. customThe solid obtained
  4. washwashed with water (2×10 cc) and ethanol (2×10 cc)
  5. customAfter 2 recrystallizations in dimethylformamide (10 cc each time)

Quellen und Nachweise

ORD-Eintrag
ord-86f51b4aa94f4fa0959685c631bcb861
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053509

Verknüpfte Notizen

Wird geladen…