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

HRID 20090

Reaction equation

HRID 20090 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-07e2c95b9113410dad05848fffb4a7be
Source dataset
uspto-grants-2010_06
Patent number
US07745427B2

Linked notes

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