Phenyl chloroformate → 1-Benzenesulfonyl-3-(1-phenoxycarbonyl4-piperazinyl)-1H-indazole

HRID 2270012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2270012
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][N:22](C)[CH2:21][CH2:20]3)=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>ClCCl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([N:19]3[CH2:24][CH2:23][N:22]([C:27]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:28])[CH2:21][CH2:20]3)=[N:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 15891Phenyl chloroformateHCID 148234251-(Benzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indazole

Produkt 1

HCID 184672231-Benzenesulfonyl-3-(1-phenoxycarbonyl4-piperazinyl)-1H-indazoleAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-benzenesulfonyl-3-(1-methyl-4-piperazinyl)-1H-indazole (2.1 g, 5.89 mmol) in dichloromethane (100 ml) was added phenyl chloroformate (3.8 ml, 29.45 mmol) at room temperature. The reaction mixture was warmed to reflux for 2 hours, cooled to room temperature, and concentrated. The residue was diluted with ethyl acetate, filtered and purified via flash column chromatography (silica gel, ethyl acetate). Concentration of the product containing fractions gave an oil which solidified on standing. The product was washed well with heptane to give 1.5 g of a white solid, m.p. 112°-114° C.

Aufarbeitung

  1. temperatureThe reaction mixture was warmed
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated
  4. additionThe residue was diluted with ethyl acetate
  5. filtrationfiltered
  6. custompurified via flash column chromatography (silica gel, ethyl acetate)
  7. additionConcentration of the product containing fractions
  8. customgave an oil which
  9. washThe product was washed well with heptane

Quellen und Nachweise

ORD-Eintrag
ord-d6a9ff22b7e84b129c9796a9ce56351c
Quelldatensatz
uspto-grants-2001_12
Patentnummer
USRE037478E1

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