Reaktion #339909

Reaktionsgleichung

N-[5-(5-Amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

Diphenylphosphoryl azide

2,4-dimethylthiazole-5-carboxylic acid

triethylamine

→

title compound

Ausbeute 45.0%

N-(5-{6-Chloro-5-[3-(2,4-dimethyl-1,3-thiazol-5-yl)ureido]pyridin-3-yl}-4-methyl-1,3-thiazol-2-yl)acetamide

Ausbeute 45.0%

Lösungsmittel

1,4-dioxane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to room temperature
2. 2
   Einengenconcentrated by evaporation
3. 3
   SonstigeThe residue was purified by preparative HPLC

Vorschrift

Diphenylphosphoryl azide (0.228 mL) was added to a stirred mixture of 2,4-dimethylthiazole-5-carboxylic acid (137 mg), triethylamine (0.148 mL) and toluene (3 mL) and the resultant mixture was heated to 100° C. for 1 hour. N-[5-(5-Amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (100 mg) was added followed by 1,4-dioxane (3 mL) and the resultant solution was stirred and heated to 100° C. for 2 hours. The mixture was cooled to room temperature and concentrated by evaporation. The residue was purified by preparative HPLC. There was thus obtained the title compound as a white solid (69 mg, 45%); 1H NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 2.27 (s, 3H), 2.39 (s, 3H), 2.54 (s, 3H), 8.17 (s, 1H), 8.65 (s, 1H), 8.82 (s, 1H), 9.75 (s, 1H); Mass Spectrum: M+H+ 437.

Quelle