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Ammonia → 1-[(5-Chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-2-yl)pyrimidin-2-yl]carbonyl]piperazine

HRID 352922
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 352922
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=4)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[O:9])=[N:6][CH:7]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Sn](CCCC)(CCCC)CCCC.C(OCC)(=O)C.N>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:28][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([S:16]([N:13]1[CH2:14][CH2:15][N:10]([C:8]([C:5]3[N:4]=[CH:3][C:2]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=4)=[CH:7][N:6]=3)=[O:9])[CH2:11][CH2:12]1)(=[O:18])=[O:17])=[CH:27]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 6077842-(Tributylstannyl)pyridineHCID 227095721-[(5-Bromopyrimidin-2-yl)carbonyl]-4-[(5-chloroindol-2-yl)sulfonyl]piperazine

Produkt 1

HCID 227103331-[(5-Chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-2-yl)pyrimidin-2-yl]carbonyl]piperazineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

At room temperature, 1-[(5-bromopyrimidin-2-yl)carbonyl]-4-[(5-chloroindol-2-yl)sulfonyl]piperazine (500 mg) and (pyridin-2-yl)tributyltin (418 mg) were dissolved in N,N-dimethylformamide (10 ml). To the reaction mixture was added tetrakis(triphenylphosphine)palladium(0) (69 mg), followed by stirring at 100° C. for 9 hours. After cooling to room temperature, ethyl acetate and ammonia solution were added. The resulting mixture was separated by ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate. The filtrate was concentrated and the residue was purified by chromatography on a silica gel column (4% methanol—methylene chloride). The resulting fraction was added with ethanol, followed by concentration. Diethyl ether was then added to the concentrate. Colorless powder thus precipitated was collected by filtration and dried, whereby the free form (254 mg) of the title compound was obtained. The resulting free form was dissolved in methylene chloride, followed by the addition of 1N hydrochloric acid (in ethanol) to make the solution acidic. After concentration, ethyl acetate and diethyl ether were added, followed by concentration. Colorless powder thus precipitated was collected by filtration and dried, whereby the title compound was obtained.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customThe resulting mixture was separated by ethyl acetate and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography on a silica gel column (4% methanol—methylene chloride)
  6. additionThe resulting fraction was added with ethanol
  7. concentrationfollowed by concentration
  8. additionDiethyl ether was then added to the concentrate
  9. customColorless powder thus precipitated
  10. filtrationwas collected by filtration
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-16457dc646ad43f79aae94216faff5f2
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06747023B1

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