p-Bromobenzenesulfonyl chloride → 4-Bromo-N-[2-chloro-5-(cis-3,5-dimethyl-1-piperazinyl)phenyl]benzenesulfonamide

HRID 130423

Reaktionsgleichung

Reaktionsgleichung von HRID 130423
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[CH:11][C:12]([Cl:16])=[C:13]([CH:15]=2)[NH2:14])[CH2:3]1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1.ClCCl>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:14][C:13]2[CH:15]=[C:9]([N:4]3[CH2:5][C@H:6]([CH3:8])[NH:7][C@H:2]([CH3:1])[CH2:3]3)[CH:10]=[CH:11][C:12]=2[Cl:16])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 590070785-(cis-3,5-Dimethyl-1-piperazinyl)-2-chloroaniline

Produkt 1

HCID 590070904-Bromo-N-[2-chloro-5-(cis-3,5-dimethyl-1-piperazinyl)phenyl]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21875418Pyridine methylene chlorideLösungsmittel

Versuchsvorschrift

A solution of 5-(cis-3,5-dimethyl-1-piperazinyl)-2-chloroaniline (D34) (108 mg, 0.45 mmol) in pyridine:dichloromethane (1:1, 4 ml) was treated with 4-bromobenzenesulfonyl chloride (138 mg, 0.54 mmol). The solution was stirred at room temperature for 2 hours, quenched with methanol and concentrated in vacuo. The residue was applied to a SCX cartridge (Varian bond-elute, 5 g) and washed with methanol and 2M ammonia in methanol. The combined basic fractions were concentrated in vacuo and the resulting residue was purified by column chromatography (FlashMaster) (dichloromethane to 5% methanol:dichloromethane) to afford some pure product. The impure fractions were purified further by MDAP, and combined with the above pure product to afford the title product (D35). MS (ES+) m/e 458/460/462 [M+H]+.

Aufarbeitung

  1. customquenched with methanol
  2. concentrationconcentrated in vacuo
  3. washwashed with methanol and 2M ammonia in methanol
  4. concentrationThe combined basic fractions were concentrated in vacuo
  5. customthe resulting residue was purified by column chromatography (FlashMaster) (dichloromethane to 5% methanol:dichloromethane)
  6. customto afford some pure product
  7. customThe impure fractions were purified further by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-f07f4d9910774fc9810990896b77eba6
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381728B2

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