Reaktion #48368

Reaktionsgleichung

Carbonyldiimidazole

2-amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino]-6-methoxypyridine

→

title compound

5-Methoxy-2-oxo-1-(1-t-butoxycarbonylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas consumed
2. 2
   workup.ADDITIONMethanol was added to the reaction
3. 3
   workup.STIRRINGthe solution stirred for several hours
4. 4
   Sonstigethe solvent was evaporated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
6. 6
   Waschenwashed with water and saturated brine
7. 7
   Trocknendried over magnesium sulfate
8. 8
   SonstigeThe crude product was purified by chromatography (silica gel, 2.5% to 5% methanol in methylene chloride gradient elution), which

Vorschrift

Carbonyldiimidazole (1.6 g, 9.8 mmol) was added to a solution of 2-amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino]-6-methoxypyridine (1.29 g, 4.00 mmol) in acetonitrile (100 mL) at room temperature. The reaction was stirred until all the starting material was consumed. Methanol was added to the reaction and the solution stirred for several hours, then the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with water and saturated brine, and then dried over magnesium sulfate. The crude product was purified by chromatography (silica gel, 2.5% to 5% methanol in methylene chloride gradient elution), which gave the title compound. MS 349 (M+1) 1H NMR (500 MHz, CDCl3) δ 8.50 (br s, 1H), 7.29 (d, J=8 Hz, 1H), 6.43 (d, J=8 Hz, 1H), 4.46 (m, 1H), 4.31 (br s, 2H), 3.90 (s, 3H), 2.85 (br s, 2H), 2.13 (m, 2H), 1.85 (d, J=12 Hz, 2H), 1.50 (s, 9H).

Quelle