Piperidine → HCID 178469543, compound

HRID 402600Notes

Reaction equation

HRID 402600 reaction equation
[O:1]=[C:2]1[CH2:6][O:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[C:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][N:26]=2)[C:21]([CH:28]=O)=[CH:20]1.N1CCCCC1>C(O)C>[NH:19]1[C:27]2=[N:26][CH:25]=[CH:24][CH:23]=[C:22]2[C:21]([CH:28]=[C:6]2[O:5][C:4]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)=[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:2]2=[O:1])=[CH:20]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 14269247HCID 14269247, compound

Product 1

HCID 178469543HCID 178469543, compoundYield 2.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-oxo-2-(2-pyridinylamino)-4,5-dihydrofuran-3-carboxylate (0.080 g, 0.32 mmol) which similarly prepared according to the procedure described in the Example 4, First step and 7-azaindole-3-carboxaldehyde (0.047 g, 0.32 mmol) in ethanol (2.0 mL), piperidine (0.038 mL, 0.39 mmol) was added at ambient temperature. The mixture was refluxed for 10 h. Cooled to ambient temperature, the precipitate was removed by filtration and the filtrate was purified by preparative HPLC to afford the titled compound as solid (0.0030 g, y. 2.5%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 10 h
  3. customthe precipitate was removed by filtration
  4. customthe filtrate was purified by preparative HPLC

Sources & evidence

ORD record
ord-578b9c9af2db43dea38230442d92b449
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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