Water → Ethyl 4-(3-(4-acetyl-1-piperazinyl)-phenyl)-amino-6-fluoro-3-nitrobenzoate

HRID 480002

Reaktionsgleichung

Reaktionsgleichung von HRID 480002
[F:1][C:2]1[CH:12]=[C:11](F)[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:17]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=2)N)[CH2:22][CH2:21]1)(=[O:19])[CH3:18].C([N:35](CC)CC)C.O>CN1C(=O)CCC1>[C:17]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:27]=[C:28]([C:11]3[CH:12]=[C:2]([F:1])[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:9]([NH2:35])[C:10]=3[N+:14]([O-:16])=[O:15])[CH:30]=[CH:31][CH:32]=2)[CH2:22][CH2:21]1)(=[O:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 111175391-[4-(3-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoate

Produkt 1

HCID 86592319Ethyl 4-(3-(4-acetyl-1-piperazinyl)-phenyl)-amino-6-fluoro-3-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl 2,4difluoro-5-nitrobenzoate (22) (1.0 g; 4.33 mmol), 4f (0.95 g; 4.33 mmol) and triethylamine (0.6 ml; 0.33 mmol) in anhydrous NMP (10 ml) was heated to 80° C. for one hour. The cooled mixture was poured into water and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate, concentrated under reduced pressure and purified by column-chromatography on silica gel using ethyl acetate as the eluent. Yield: 1.53 g (82%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column-chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f60e53fbf16d4216930254366e7b9374
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649609B2

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