反応 #48368

反応方程式

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

溶媒

acetonitrile

反応条件

後処理

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

実験手順

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).

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