L-Proline → HCID 178469950, compound

HRID 402710Notes

Reaction equation

HRID 402710 reaction equation
[O:1]=[C:2]1[CH2:6][O:5][C:4]([NH:7][N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]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.N1CCC[C@H]1C(O)=O>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][N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]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 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708403HCID 86708403, compound

Product 1

HCID 178469950HCID 178469950, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-oxo-2-(N-piperidinoamino)-4,5-dihydrofuran-3-carboxylate (0.25 g, 0.98 mmol) which similarly prepared according to the procedure described in the Example 74, Fourth step and 7-azaindole-3-carboxaldehyde (0.14 g, 0.98 mmol) in ethanol (10 mL), L-proline (0.011 mg, 0.096 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 ethanol and diethyl ether then dried to afford the titled compound as solid (0.015 g, y. 4%).

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 ethanol and diethyl ether
  5. customthen dried

Sources & evidence

ORD record
ord-a8f94a3754824f798a5e7a390124d1de
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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