Reacción #2328988

Ecuación de reacción

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

Disolventes

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente