Réaction #77681

Équation de réaction

2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamine

toluene-4-sulfonic acid 2-(6-acetylamino-pyridin-3-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

diisopropyl ethyl amine

→

desired product

Rendement 45.0%

(R)-N-[5-(1-(tert-Butyl-dimethyl-silanyloxy)-2-{2-[4-(2-methyl-thiazol-4-yl)-phenoxy]ethylamino}-ethyl)-pyridin-2-yl]-acetamide

Rendement 45.0%

Solvants

dimethylsulfoxide

Conditions de réaction

Traitement

1. 1
   Autrewas then partitioned between diethyl ether and water
2. 2
   ExtractionThe aqueous phase was extracted with diethyl ether four times
3. 3
   Lavagethe combined organic extracts were then washed with brine
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutreThe resulting white solid was purified by column chromatography (methylene chloride to 10% methanol/methylene chloride)

Mode opératoire

In a round-bottomed flask, 2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamine (175 mg, 0.747 mmol) and toluene-4-sulfonic acid 2-(6-acetylamino-pyridin-3-yl)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester (231 mg, 0.498 mmol) were dissolved in dimethylsulfoxide (0.50 mL), and diisopropyl ethyl amine (0.105 mL, 0.600 mmol) was added in one portion. The resulting mixture was heated to about 80° C. for about sixteen hours, and was then partitioned between diethyl ether and water. The aqueous phase was extracted with diethyl ether four times, and the combined organic extracts were then washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting white solid was purified by column chromatography (methylene chloride to 10% methanol/methylene chloride) to afford 117 mg (45%) of the desired product. LRMS ([M+1]+): 527.1.

Source