Piperidine → HCID 178469515, compound

HRID 402592Notes

Reaction equation

HRID 402592 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[C:3]([CH:10]=O)=[CH:2]1.[O:12]=[C:13]1[CH2:17][O:16][C:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:14]1[C:25]([O:27][CH2:28][CH3:29])=[O:26].N1CCCCC1>C(O)C>[NH:1]1[C:9]2=[N:8][CH:7]=[CH:6][CH:5]=[C:4]2[C:3]([CH:10]=[C:17]2[O:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:14]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:13]2=[O:12])=[CH:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 698491Ethyl 2-anilino-4-oxo-4,5-dihydrofuran-3-carboxylateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 178469515HCID 178469515, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-azaindole-3-carboxaldehyde (0.10 g, 0.70 mmol) and ethyl 4-oxo-2-(phenylamino)-4,5-dihydrofuran-3-carboxylate (0.18 g, 0.70 mmol) in ethanol (3.0 mL), piperidine (0.083 mL, 0.84 mmol) was added at ambient temperature. The mixture was refluxed for 12 h. Cooled to ambient temperature, the precipitate was collected by filtration, washed with cold ethanol and isopropyl ether then dried to afford the titled compound (0.13 g, y. 48%).

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with cold ethanol and isopropyl ether
  4. customthen dried

Sources & evidence

ORD record
ord-687f711a574048b58a672c0728ba642c
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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