Piperidine → HCID 178469577, compound

HRID 402675Notes

Reaction equation

HRID 402675 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][NH: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]([NH: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 86708377HCID 86708377, compound

Product 1

HCID 178469577HCID 178469577, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-[(4-{[2-(dimethylamino)ethyl]amino}-2-methylphenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.27 g, 0.70 mmol) which similarly prepared according to the procedure described in the Example 125, First step to Third step and 7-azaindole-3-carboxaldehyde (0.11 g, 0.70 mmol) in ethanol (5.0 mL), piperidine (0.10 mL, 1.0 mmol) was added at ambient temperature. The mixture was refluxed for 16 h. Cooled to ambient temperature, the solvent was removed under reduced pressure then the residue was purified by preparative HPLC to afford the titled compound as solid (0.015 g, y. 8%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 16 h
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a86a57b8a62745df9a60d641916849e7
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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