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4-(Thiophen-2-yl)benzene-1-sulfonyl chloride → N-[3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)phenyl]-4-(2-thienyl)benzenesulfonamide

HRID 130434
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 130434
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[NH2:12])[CH2:3]1.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>N1C=CC=CC=1.ClCCl.ClCCl>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[C:11]([NH:12][S:29]([C:26]3[CH:25]=[CH:24][C:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)=[CH:28][CH:27]=3)(=[O:30])=[O:31])[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 183877594-(Thiophen-2-yl)benzene-1-sulfonyl chlorideHCID 590070453-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)aniline

Produkt 1

HCID 11518200N-[3-(cis-3,5-Dimethyl-1-piperazinyl)-4-(methyloxy)phenyl]-4-(2-thienyl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel
HCID 21875418
Pyridine methylene chloride
Lösungsmittel

Versuchsvorschrift

A solution of 3-(cis-3,5-dimethyl-1-piperazinyl)-4-(methyloxy)aniline (D2) (117 mg, 0.5 mmol) in pyridine:dichloromethane (1:1, 4 ml) was treated with a solution 4-(2-thienyl)benzenesulfonyl chloride (WO 9827069) (143 mg, 0.55 mmol) in dichloromethane (2 ml). The solution was stirred at room temperature for 24 hours, quenched with methanol (2 ml) and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with water (×3). The organic phase 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 (dichloromethane to 1:4 2M ammonia in methanol:dichloromethane) to afford the title product (E11). MS (ES+) m/e 458 [M+H]+.

Aufarbeitung

  1. customquenched with methanol (2 ml)
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water (×3)
  5. washwashed with methanol and 2M ammonia in methanol
  6. concentrationThe combined basic fractions were concentrated in vacuo
  7. customthe resulting residue was purified by column chromatography (dichloromethane to 1:4 2M ammonia in methanol:dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-c605a5a7a06b49218e76290c326b7258
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07381728B2

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