Reacción #2328989

Ecuación de reacción

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

HCl

→

title compound

Rendimiento 22.8%

2-[6-(Methylamino)pyridin-3-yl]-1,3-benzoxazol-6-ol

Rendimiento 22.8%

Disolventes

diethylether

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed in vacuo and hydrogen bromide (48% aq., 2 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Extracciónextracted twice with ethyl acetate
4. 4
   LavadoThe combined organic layers were washed with brine
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated in vacuo
8. 8
   OtroThe crude product was purified by preparative HPLC

Procedimiento

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N-methylpyridin-2-amine (50 mg, 0.20 mmol) was dissolved in CH2Cl2 (10 mL) and made acidic with 2M HCl in diethylether. The solvent was removed in vacuo and hydrogen bromide (48% aq., 2 mL) was added. The reaction was run in a microwave reactor at 120° C. for 15 minutes. The mixture was then made basic with sodium bicarbonate and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by preparative HPLC, to give the title compound (11 mg) as a white solid. 1H NMR δ ppm 9.95 (br. s, 1H) 8.72 (d, 1H) 7.99 (dd, 1H) 7.46 (d, 1 H) 7.28 (d, 1 H) 7.03 (d, 1H) 6.79 (dd, 1H) 6.58 (d, 1H) 2.85 (d, 3H); MS m/z (M+H) 242, (M−H) 240.

Fuente