1,1'-Carbonyldiimidazole → tert-Butyl 4-(6-fluoro-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate

HRID 1671584Notes

Reaction equation

HRID 1671584 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][C:17]([F:34])=[CH:16][N:15]=1>C(#N)C>[F:34][C:17]1[CH:18]=[C:19]2[N:20]([CH:21]3[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH2:25][CH2:26]3)[C:1](=[O:2])[NH:13][C:14]2=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22293195HCID 22293195, compound

Product 1

HCID 22293159tert-Butyl 4-(6-fluoro-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylateYield 39.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Carbonyldiimidazole (1.53 g, 9.41 mmol) was added to a solution of tert-butyl 4-[(2-amino-5-fluoropyridin-3-yl)amino]piperidine-1-carboxylate (0.73 g, 2.35 mmol) in acetonitrile (10 mL) at room temperature. The reaction was stirred until all the starting material was consumed (approximately 2 h) and then the solvent was evaporated in vacuo. The residue was diluted with water, extracted with dichloromethane (3×), dried over magnesium sulfate and then concentrated. The crude product was purified by chromatography (silica gel, 1% to 10% methanol in methylene chloride gradient elution), which gave the title compound (0.309 g). MS 337.2 (M+1)

Workup

  1. customwas consumed (approximately 2 h)
  2. customthe solvent was evaporated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with dichloromethane (3×)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (silica gel, 1% to 10% methanol in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-b17465ead5cf4fd3ba0ff2c2bb4dbe0f
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

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