(S)-2-(2-Methoxyethyl)piperazine → (S)-7-Chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131457

Reaktionsgleichung

Reaktionsgleichung von HRID 131457
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[S:9][C:10]([CH3:16])=[CH:11][C:12]=3[C:13]([NH2:15])=[N:14][C:5]=2[CH:4]=1.[CH3:19][O:20][CH2:21][CH2:22][C@H:23]1[CH2:28]N[CH2:26][CH2:25][NH:24]1>CS(C)=O.C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[S:9][C:10]([CH3:16])=[CH:11][C:12]=3[C:13]([N:15]3[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:22][CH2:21][O:20][CH3:19])[CH2:28]3)=[N:14][C:5]=2[CH:4]=1

Komponenten

6

Edukt 2

HCID 55287560(S)-2-(2-Methoxyethyl)piperazineHCID 1363885727-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

Produkt 1

HCID 136090361(S)-7-Chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azuleneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 22340214Dimethylsulfoxide tolueneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Dissolve 7-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (1.46 g, 4.86 mmol) and (S)-2-(2-methoxy-ethyl)-piperazine (2.1 g, 14.6 mmol) in dimethylsulfoxide/toluene (1:2)(18 ml), stir under nitrogen and heat in an oil bath at 130° C. for 28.5 hours. Stir 16 hours at ambient temperature. Dilute the mixture with water and ethyl acetate, and extract with ethyl acetate. Combine the ethyl acetate extracts, wash with water and brine, dry the organic phase (Na2SO4), filter and concentrate under reduced pressure. Chromatograph on silica gel (eluent: 0-10% 2N ammonia in methanol/dichloromethane) to give the title compound (1.14 g, 60%), Mass Spectrum (ESMS) 391/393 (M+1), mp 179-183° C. (dec).

Aufarbeitung

  1. stirringStir 16 hours at ambient temperature
  2. extractionextract with ethyl acetate
  3. washwash with water and brine
  4. dry with materialdry the organic phase (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0de79bc9bdcf4decb9130433baa099b5
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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