Piperidine → HCID 178469579, compound

HRID 402625Notes

Reaction equation

HRID 402625 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[O:17][CH2:18][C:19](=[O:26])[C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][N:34]=2)[C:29]([CH:36]=O)=[CH:28]1.N1CCCCC1>C(O)C>[NH:27]1[C:35]2=[N:34][CH:33]=[CH:32][CH:31]=[C:30]2[C:29]([CH:36]=[C:18]2[O:17][C:16]([NH:15][C:12]3[CH:13]=[CH:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:10][CH:11]=3)=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]2=[O:26])=[CH:28]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708316HCID 86708316, compound

Product 1

HCID 178469579HCID 178469579, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-({4-[(tert-butoxycarbonyl)amino]phenyl}amino)-4-oxo-4,5-dihydrofuran-3-carboxylate (0.32 g, 0.88 mmol) which similarly prepared according to the procedure described in the Example 4, First step and 7-azaindole-3-carboxaldehyde (0.13 g, 0.88 mmol) in ethanol (5.0 mL), piperidine (0.18 mL, 1.8 mmol) was added at ambient temperature. The mixture was refluxed for 16 h. Cooled to ambient temperature, the precipitate was collected by filtration, washed with ethanol then dried to afford ethyl 5-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-2-({4-[(tert-butoxycarbonyl)amino]phenyl}amino)-4-oxo-4,5-dihydrofuran-3-carboxylate as solid (0.095 g, y. 21%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 16 h
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethanol
  5. customthen dried

Sources & evidence

ORD record
ord-2dab1ee63b684ebbb2dccf93d03dea69
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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