1,1'-Carbonyldiimidazole → 5-Methoxy-2-oxo-1-(1-t-butoxycarbonylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine

HRID 271886

Reaktionsgleichung

Reaktionsgleichung von HRID 271886
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[C:19]([NH:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[CH:18][CH:17]=[C:16]([O:34][CH3:35])[N:15]=1>C(#N)C>[CH3:35][O:34][C:16]1[N:15]=[C:14]2[NH:13][C:1](=[O:2])[N:20]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:23][CH2:22]3)[C:19]2=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 222931662-Amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino)-6-methoxypyridine

Produkt 1

HCID 222932805-Methoxy-2-oxo-1-(1-t-butoxycarbonylpiperidin-4-yl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customwas consumed
  2. additionMethanol was added to the reaction
  3. stirringthe solution stirred for several hours
  4. customthe solvent was evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe crude product was purified by chromatography (silica gel, 2.5% to 5% methanol in methylene chloride gradient elution), which

Quellen und Nachweise

ORD-Eintrag
ord-0be740d13e324469be16d45c23dd20a8
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452903B2

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