L-Proline → HCID 178469775, compound

HRID 402633Notes

Reaction equation

HRID 402633 reaction equation
[CH:1]([NH:4][C:5]1[O:6][CH2:7][C:8](=[O:15])[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])([CH3:3])[CH3:2].[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][N:23]=2)[C:18]([CH:25]=O)=[CH:17]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:16]1[C:24]2=[N:23][CH:22]=[CH:21][CH:20]=[C:19]2[C:18]([CH:25]=[C:7]2[O:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]2=[O:15])=[CH:17]1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 14198525HCID 14198525, compound

Product 1

HCID 178469775HCID 178469775, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(isopropylamino)-4-oxo-4,5-dihydrofuran-3-carboxylate (0.50 g, 2.3 mmol) which similarly prepared according to the procedure described in the Example 4, First step and 7-azaindole-3-carboxaldehyde (0.34 g, 2.3 mmol) in ethanol (15 mL), L-proline (0.027 g, 0.23 mmol) was added at ambient temperature. The mixture was refluxed for 16 h. Cooled to ambient temperature, the precipitate was collected by filtration, washed with ethanol then dried to afford the titled compound as solid (0.45 g, y. 56%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 16 h
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethanol
  5. customthen dried

Sources & evidence

ORD record
ord-202f542abcc540d38019fdc25ff44ad0
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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