1,1'-Carbonyldiimidazole → tert-butyl 4-{2-oxo-1H,2H,3H-imidazo[4,5-b]pyridin-1-yl}piperidine-1-carboxylate

HRID 1453931Notes

Reaction equation

HRID 1453931 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]=[CH:16][N:15]=1>C(#N)C>[O:2]=[C:1]1[NH:13][C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[N:20]1[CH:21]1[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 22293217tert-Butyl 4-[(2-aminopyridin-3-yl)amino]piperidine-1-carboxylate

Product 1

HCID 22293220tert-butyl 4-{2-oxo-1H,2H,3H-imidazo[4,5-b]pyridin-1-yl}piperidine-1-carboxylateYield 87.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Carbonyldiimidazole (0.70 g, 4.33 mmol) was added to a solution of 2-amino-3-[(1-t-butoxycarbonylpiperidin-4-yl)amino]pyridine (1.15 g, 3.93 mmol) in acetonitrile (150 mL) at room temperature. After several hours, an additional amount of carbonyldiimidazole was added (0.81 g), and the reaction stirred overnight. The acetonitrile was evaporated in vacuo, the residue partitioned between water and chloroform, and the organic phase washed with saturated brine and dried over magnesium sulfate. The crude product was purified by chromatorgraphy (silica gel, 1.2 to 2.5% methanol in methylene chloride gradient elution), which gave the title compound (1.09 g). 1H NMR (500 MHz, CDCl3) δ 9.39 (br s, 1H), 8.04 (dd, J=1, 5 Hz, 1H), 7.33 (dd, J=1, 8 Hz, 1H), 6.99 (dd, J=5, 8 Hz, 1H), 4.50 (m, 1H), 4.32 (br s, 2H), 2.86 (br s, 2H), 2.20 (m, 2H), 1.86 (d, J=12 Hz, 2H), 1.50 (s, 9H).

Workup

  1. waitAfter several hours
  2. customThe acetonitrile was evaporated in vacuo
  3. customthe residue partitioned between water and chloroform
  4. washthe organic phase washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by chromatorgraphy (silica gel, 1.2 to 2.5% methanol in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-c886e365a21f45a6abed29606de08bc4
Source dataset
uspto-grants-2009_01
Patent number
US07476665B2

Reaction notes

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