Réaction #2328989

Équation de réaction

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

HCl

→

title compound

Rendement 22.8%

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

Rendement 22.8%

Solvants

diethylether

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was removed in vacuo and hydrogen bromide (48% aq., 2 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Extractionextracted twice with ethyl acetate
4. 4
   LavageThe combined organic layers were washed with brine
5. 5
   Séchagedried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated in vacuo
8. 8
   AutreThe crude product was purified by preparative HPLC

Mode opératoire

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.

Source