2-(4-Fluorophenyl)piperazine → (RS)-1-cyclopropyl-7-fluoro-8-[3-(4-fluorophenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid

HRID 344858

Reaktionsgleichung

Reaktionsgleichung von HRID 344858
Cl[C:2]1[C:3]([F:23])=[CH:4][C:5]2[C:6]([CH:22]=1)=[N:7][C:8]1[N:9]([CH:19]3[CH2:21][CH2:20]3)[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:36][NH:35][CH2:34][CH2:33][NH:32]2)=[CH:27][CH:26]=1>C(N(CC)CC)C>[CH:19]1([N:9]2[C:8]3[N:7]=[C:6]4[CH:22]=[C:2]([N:35]5[CH2:34][CH2:33][NH:32][CH:31]([C:28]6[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=6)[CH2:36]5)[C:3]([F:23])=[CH:4][C:5]4=[CH:14][C:13]=3[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)[CH2:21][CH2:20]1

Komponenten

4

Edukt 2

HCID 46176232-(4-Fluorophenyl)piperazineHCID 147005568-Chloro-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

Produkt 1

HCID 54113196(RS)-1-cyclopropyl-7-fluoro-8-[3-(4-fluorophenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acidAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

(RS)-1-Cyclopropyl-7-fluoro-8-[3-(4-fluorophenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 11 below, but starting with 8-chloro-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid (2 g), (RS)-2-(4-fluorophenyl)piperazine (6.534 g) and triethylamine (9 cc). The reaction mixture is concentrated under reduced pressure (20 kPa) at a temperature in the region of 60° C. The dry extract is taken up with water (20 cc) and acetic acid (0.5 cc). The insoluble matter is drained and washed with water (2×5 cc). After 1 recrystallization in a mixture of dimethylformamide (37 cc) and ethanol (37 cc), (RS)-1-cyclopropyl-7-fluoro-8-[3-(4-fluorophenyl) -1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid (1.07 g) is obtained in the form of a yellow solid, m.p. 306° C.

Aufarbeitung

  1. custom(RS)-1-Cyclopropyl-7-fluoro-8-[3-(4-fluorophenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine-3-carboxylic acid was prepared under the conditions of Example 11 below, but
  2. concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at a temperature in the region of 60° C
  3. extractionThe dry extract
  4. washwashed with water (2×5 cc)
  5. customAfter 1 recrystallization
  6. additionin a mixture of dimethylformamide (37 cc) and ethanol (37 cc)

Quellen und Nachweise

ORD-Eintrag
ord-ee99b5e416e14f229e0397530b9cac43
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05053509

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