Reaktion #306913

Reaktionsgleichung

2-fluoro-benzoic acid

4-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butylamine

diisopropylethylamine

hydroxybenzotriazole

N-ethyl-N′-(3-dimethylaminopropyl)-carbodiimide hydrochloride

→

title compound

Ausbeute 88.5%

N-{4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}-2-fluoro-benzamide

Ausbeute 88.5%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe organic layer washed with aqueous saturated sodium chloride
2. 2
   Extraktionthe aqueous phase re-extracted once with dichloromethane
3. 3
   Trocknenthe combined organic phases were dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated to dryness
6. 6
   SonstigeThe crude product was purified by chromatography on silica gel
7. 7
   workup.ADDITIONFractions containing the product
8. 8
   SonstigeThe solvent was evaporated

Vorschrift

0.29 g of 2-fluoro-benzoic acid (2.03 mmol) and 0.7 g of 4-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butylamine (2.03 mmol) were dissolved in 25 ml of dichloromethane. 1.04 g of diisopropylethylamine (8.04 mmol), 0.19 g of hydroxybenzotriazole (HOBt, 1.4 mmol), and 0.46 g of N-ethyl-N′-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDCl, 2.4 mmol) were added at 0° C. and the reaction mixture was stirred for 16 h at room temperature. 25 ml of dichloromethane were added, the organic layer washed with aqueous saturated sodium chloride, the aqueous phase re-extracted once with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel using ethyl acetate and ethyl acetate-methanol (5%). Fractions containing the product were combined. The solvent was evaporated to yield 0.84 g of the title compound as a white solid.

Quelle