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

HRID 1172292Notes

Reaction equation

HRID 1172292 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=[CH:4][N:3]=1.C1N=CN([C:27](N2C=NC=C2)=[O:28])C=1>CC#N>[O:28]=[C:27]1[NH:1][C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[N:8]1[CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 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 108.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-Butyl 4-(2-aminopyridin-3-ylamino)piperidine-1-carboxylate (3.0 g, 10.3 mmol) in CH3CN (206 ml) at RT was added CDI (4.2 g, 25.7 mmol) in portions and the reaction mixture was stirred at RT for 16 hours. The reaction mixture was evaporated to dryness and the residue was take up in DCM and water. The layers were separated and the organic layer was washed with brine, dried (Na2SO4) and evaporated to dryness. Purification by column chromatography (1-10% MeOH in DCM) gave the desired solid as a beige solid (3.55 g). LC/MS (10% to 99%): M/Z (M+H)+ (obs)=319; tR=2.31.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customPurification by column chromatography (1-10% MeOH in DCM)

Sources & evidence

ORD record
ord-19883c05a42149cb90b94c9d994f5fca
Source dataset
uspto-grants-2010_11
Patent number
US07834000B2

Reaction notes

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