Potassium Carbonate → HCID 86620414, compound

HRID 252737Notes

Reaction equation

HRID 252737 reaction equation
[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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 280907N-(4-Methylthiazol-2-yl)acetamideHCID 6407597N-(6-chloropyridazin-3-yl)benzenesulfonamide

Product 1

HCID 86620414HCID 86620414, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 178454878HCID 178454878, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bd30feff0fd84b658f975a5142feb62a
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

Loading…