4-Chlorobenzenesulfonyl chloride → HCID 18697990, Verbindung

HRID 2289544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2289544
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[N:23]=3)[CH2:18][CH2:17]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(N(CC)CC)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1>ClCCl>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([S:43]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[N:23]=4)[CH2:18][CH2:17]3)=[O:15])[CH2:10][CH2:9]2)(=[O:45])=[O:44])=[CH:39][CH:38]=1

Komponenten

5

Edukt 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 18697989HCID 18697989, Verbindung

Produkt 1

HCID 18697990HCID 18697990, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(tert-butoxycarbonyl)-4-(1-(2-methylpyrimidin-4-yl)piperazin-4-ylcarbonyl)piperazine (700 mg) was stirred in dichloromethane (20 ml) and triethylarnine (1.34 ml) and cooled in an ice-bath. 4-chlorobenzenesulphonylchloride (0.56 g) was added and reaction allowed to warm to room temperature and then stirred overnight. The mixture was evaporated and the residue was purified by chromatography on silica gel using in gradient of dichloromethane to 8% methanol in dichloromethane as eluent to give a foam. This was triturated with diethylether to give 1-(4-chlorophenylsulphonyl)-4-[1-(2-methylpyrimidin-4-yl)piperazin-4-ylcarbonyl]piperazine a colourless solid 1.05 g ;m.p. 183-184° C.; NMR (CDCl3): 8.15 (m, 1H), 7.7 (m, 2H), 7.55 (m, 2H), 6.3 (m, 1H), 3.65 (m, 4H), 3.45 (m, 4H), 3.35 (m, 4H), 3.05 (m, 4H), 2.5 (s, 3H).

Aufarbeitung

  1. customreaction
  2. customThe mixture was evaporated
  3. customthe residue was purified by chromatography on silica gel using in gradient of dichloromethane to 8% methanol in dichloromethane as eluent
  4. customto give a foam
  5. customThis was triturated with diethylether

Quellen und Nachweise

ORD-Eintrag
ord-8b4ff46da9a74baf9bde49c438fbbfa0
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06093718

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