Реакция #2328989

Уравнение реакции

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

HCl

→

title compound

Выход 22.8%

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

Выход 22.8%

Растворители

diethylether

CH2Cl2

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was removed in vacuo and hydrogen bromide (48% aq., 2 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Экстракцияextracted twice with ethyl acetate
4. 4
   ПромывкаThe combined organic layers were washed with brine
5. 5
   Сушкаdried (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated in vacuo
8. 8
   ДругоеThe crude product was purified by preparative HPLC

Методика

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.

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