Reaktion #10552

Reaktionsgleichung

6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylic acid

2,2,2-trifluoro-N-(4-piperidinyl)acetamide

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

(2S,3S,4R,5R)-5-[6-[(2,2-Diphenylethyl)amino]-2-({4-[(trifluoroacetyl)amino]-1-piperidinyl}carbonyl)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux for a further 96 hours
3. 3
   Sonstigesolvent removed by evaporation under reduced pressure
4. 4
   SonstigeThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
5. 5
   SonstigeAfter evaporation of appropriate fractions the target compound
6. 6
   Sonstigewas obtained as a white solid, (43 mg, 18%)

Vorschrift

A solution of 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylic acid (Preparation 39) (0.2 g, 0.38 mmol), 2,2,2-trifluoro-N-(4-piperidinyl)acetamide (83 mg, 0.42 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (81 mg, 0.42 mmol) in dichloromethane (5 ml) was stirred at room temperature for 48 hours and then heated under reflux for a further 96 hours. The solution was allowed to cool to room temperature and then solvent removed by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:concentrated aqueous ammonia (95:5:1, by volume) changing to dichloromethane:methanol:concentrated aqueous ammonia (80:20:1, by volume). After evaporation of appropriate fractions the target compound was obtained as a white solid, (43 mg, 18%).

Quelle