반응 #2328988

반응 방정식

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

용매

water

반응 조건

후처리

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

실험 절차

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.

출처