Reaktion #2328988

Reaktionsgleichung

sodium bicarbonate

N-(2-Hydroxy-4-methoxyphenyl)-6-(methylamino)nicotinamide

acetic acid

→

N-[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]-N-methylacetamide

title compound

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N-methylpyridin-2-amine

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous solution was extracted three times with diethyl ether
2. 2
   Waschenthe combined organic layers were washed with brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe crude product was purified first by flash column chromatography (hexane/ethyl acetate-gradient; 30-50% ethyl acetate)

Vorschrift

N-(2-Hydroxy-4-methoxyphenyl)-6-(methylamino)nicotinamide (0.23 g, 0.84 mmol) was mixed with acetic acid (4 mL) and the reaction was run in a microwave reactor at 200° C. for 25 minutes. The reaction mixture was added to water and made basic with sodium bicarbonate (sat. aq.). The aqueous solution was extracted three times with diethyl ether and the combined organic layers were washed with brine, dried (MgSO4) and evaporated. The crude product was purified first by flash column chromatography (hexane/ethyl acetate-gradient; 30-50% ethyl acetate), followed by preparative HPLC, resulting in the isolation of N-[5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-yl]-N-methylacetamide (6 mg) as a minor product, together with the title compound (0.13 g) as a solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.90 (d, 1H) 8.23 (dd, 1H) 7.59 (d, 1H) 7.10 (d, 1H) 6.94 (dd, 1H) 6.52 (d, 1H) 5.26 (br. s, 1H) 3.89 (s, 3H) 2.82-3.16 (m, 3 H); MS m/z (M+H) 256.

Quelle