Piperidine → HCID 178469512, compound

HRID 402619Notes

Reaction equation

HRID 402619 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][C:9]=2[CH3:14])=[C:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][N:27]=2)[C:22]([CH:29]=O)=[CH:21]1.N1CCCCC1>C(O)C>[NH:20]1[C:28]2=[N:27][CH:26]=[CH:25][CH:24]=[C:23]2[C:22]([CH:29]=[C:6]2[O:5][C:4]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH3:14])=[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:2]2=[O:1])=[CH:21]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708308HCID 86708308, compound

Product 1

HCID 178469512HCID 178469512, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-oxo-2-(o-tolylamino)-4,5-dihydrofuran-3-carboxylate (0.098 g, 0.38 mmol) which similarly prepared according to the procedure described in the Example 4, First step and 7-azaindole-3-carboxaldehyde (0.050 g, 0.34 mmol) in ethanol (2.0 mL), piperidine (0.0034 mL, 0.034 mmol) was added at ambient temperature. The mixture was refluxed for 32 h. The precipitate was collected by filtration, washed with hot ethanol. The solid was washed with hexane then dried to afford the titled compound as solid (0.019 g, y. 27%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 32 h
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with hot ethanol
  5. washThe solid was washed with hexane
  6. customthen dried

Sources & evidence

ORD record
ord-5d9124b5b48a4eed91734c3c5306d9c5
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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