Piperidine → HCID 178469595, compound

HRID 402663Notes

Reaction equation

HRID 402663 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[O:14][CH2:15][C:16](=[O:23])[C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([CH3:24])[CH:7]=1.[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][N:33]=2)[C:28]([CH:35]=O)=[CH:27]1.N1CCCCC1>C(O)C>[CH:18]([OH:20])=[O:19].[NH:26]1[C:34]2=[N:33][CH:32]=[CH:31][CH:30]=[C:29]2[C:28]([CH:35]=[C:15]2[O:14][C:13]([NH:12][C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:25])=[CH:7][C:8]=3[CH3:24])=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]2=[O:23])=[CH:27]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708357HCID 86708357, compound

Product 1

HCID 178469595HCID 178469595, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-({4-[2-(dimethylamino)ethoxy]-2-methylphenyl}amino)-4-oxo-4,5-dihydrofuran-3-carboxylate (0.070 g, 0.20 mmol) which similarly prepared according to the procedure described in the Example 74, Fourth step and 7-azaindole-3-carboxaldehyde (0.029 g, 0.20 mmol) in ethanol (2.0 mL), piperidine (0.020 mL, 0.20 mmol) was added at ambient temperature. The mixture was refluxed for 5 days. Cooled to ambient temperature, the precipitate was collected by filtration then purified by preparative HPLC to afford the titled compound as solid (0.016 g, y. 16%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 5 days
  3. filtrationthe precipitate was collected by filtration
  4. customthen purified by preparative HPLC

Sources & evidence

ORD record
ord-98f54f785c8941c7bb27c3e4b21a6df9
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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