Piperidine → HCID 178469601, compound

HRID 402669Notes

Reaction equation

HRID 402669 reaction equation
[OH:1][CH:2]([CH2:24][OH:25])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[O:13][CH2:14][C:15](=[O:22])[C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:7]([CH3:23])[CH:6]=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>[NH:26]1[C:34]2=[N:33][CH:32]=[CH:31][CH:30]=[C:29]2[C:28]([CH:35]=[C:14]2[O:13][C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:24][OH:25])=[CH:6][C:7]=3[CH3:23])=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15]2=[O:22])=[CH:27]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708369HCID 86708369, compound

Product 1

HCID 178469601HCID 178469601, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of ethyl 2-{[4-(2,3-dihydroxypropoxy)-2-methylphenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate (0.17 g, 0.50 mmol) which similarly prepared according to the procedure described in the Example 74, First step to Fourth step and 7-azaindole-3-carboxaldehyde (0.070 g, 0.50 mmol) in ethanol (5.0 mL), piperidine (0.10 mL, 1.0 mmol) was added at ambient temperature. The mixture was refluxed for 2 days. Cooled to ambient temperature, the precipitate was collected by filtration, washed with diethyl ether then dried to afford the titled compound as solid (0.054 g, y. 23%).

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 diethyl ether
  5. customthen dried

Sources & evidence

ORD record
ord-c1f34f0286054dd7bd36e68c2c4376f8
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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