Piperidine → HCID 178469520, compound

HRID 402614Notes

Reaction equation

HRID 402614 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][CH2:11][C:12](=[O:19])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[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:11]2[O:10][C:9]([NH:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]2=[O:19])=[CH:21]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708301HCID 86708301, compound

Product 1

HCID 178469520HCID 178469520, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-[(2-hydroxyphenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.050 g, 0.19 mmol) which similarly prepared according to the procedure described in the Example 4 and 7-azaindole-3-carboxaldehyde (0.023 g, 0.16 mmol) in ethanol (1.0 mL), piperidine (0.0010 mL, 0.010 mmol) was added at ambient temperature. The mixture was refluxed for 2 days. The precipitate was collected by filtration, washed with hot ethanol. The solid was washed hexane then dried to afford the titled compound (0.008 g, y. 11%).

Workup

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

Sources & evidence

ORD record
ord-4728a112aefd4273af90ba007ace1ef1
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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