Reaktion #1597470

Reaktionsgleichung

2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-piperidin-4-yl-phenyl)-amide

6-fluoronicotinic acid

potassium carbonate

→

4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid

Ausbeute 15.1%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with ethyl acetate and 0.1N hydrochloric acid
2. 2
   WaschenThe organic layer was washed with water and brine
3. 3
   SonstigeSolvents were evaporated
4. 4
   Sonstigethe residue was purified through ISCO column chromatography (silica gel, ethyl acetate in hexanes, 10% to 100% linear gradient)
5. 5
   EinengenThe collected fractions were concentrated
6. 6
   Filtrationthe white crystalline material was filtered

Vorschrift

A mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-piperidin-4-yl-phenyl)-amide (208 mg, 0.5 mmol) and 6-fluoronicotinic acid (72 mg, 0.5 mmol) in DMSO (2 L) containing potassium carbonate (135 mg, 1 mmol) was heated in a microwave at 135° C. for 35 minutes. The mixture was extracted with ethyl acetate and 0.1N hydrochloric acid. The organic layer was washed with water and brine. Solvents were evaporated and the residue was purified through ISCO column chromatography (silica gel, ethyl acetate in hexanes, 10% to 100% linear gradient). The collected fractions were concentrated and the white crystalline material was filtered to give 4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (40.5 mg). LC-MS for C28H23F3N4O4 (m/e) calcd 536, obsd 537 (M+H). 1H-NMR is consistent with the desired structure.

Quelle