Potassium Carbonate → HCID 86620414, Verbindung

HRID 252737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252737
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].Cl[C:12]1[N:17]=[N:16][C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[Pd+]>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:12]1[N:17]=[N:16][C:15]([NH:18][S:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:21])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2809072-Acetamido-4-methylthiazoleHCID 6407597N-(6-chloropyridazin-3-yl)benzenesulfonamide

Produkt 1

HCID 86620414HCID 86620414, VerbindungAusbeute 19,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178454878HCID 178454878, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-acetamido-4-methylthiazole (78 mg), N-(6-chloropyridazin-3-yl)benzenesulfonamide (80 mg), potassium carbonate (374 mg), palladium (I) tri-tert-butylphosphine bromide dimer (commercially available from Alfa Aesar (Johnson-Matthey company); 241 mg) and DMSO (5 mL) was purged with nitrogen. The resultant mixture was heated to 150° C. for 30 minutes. The mixture was cooled to room temperature, filtered and purified directly by preparative HPLC. There was thus obtained the title compound as a solid (23 mg); 1H NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 2.46 (s, 3H), 7.53-7.60 (m, 3H), 7.78 (m, 1H), 7.86-7.88 (m, 2H), 7.95-7.97 (br d, 1H); Mass Spectrum: M+H+ 390.

Aufarbeitung

  1. custom241 mg) and DMSO (5 mL) was purged with nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. custompurified directly by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bd30feff0fd84b658f975a5142feb62a
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868188B2

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