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

HRID 1695891Notes

Reaction equation

HRID 1695891 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-60fb1ca0a3734176b8eedab94a5db5fe
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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