L-Proline → HCID 178458501, compound

HRID 402632Notes

Reaction equation

HRID 402632 reaction equation
[O:1]=[C:2]1[CH2:6][O:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH3:17])=[CH:10][CH:9]=2)=[C:3]1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][N:30]=2)[C:25]([CH:32]=O)=[CH:24]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:23]1[C:31]2=[N:30][CH:29]=[CH:28][CH:27]=[C:26]2[C:25]([CH:32]=[C:6]2[O:5][C:4]([NH:7][C:8]3[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][CH3:17])=[CH:12][CH:13]=3)=[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]2=[O:1])=[CH:24]1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708327HCID 86708327, compound

Product 1

HCID 178458501HCID 178458501, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-oxo-2-{[4-(1-propoxy)phenyl]amino}-4,5-dihydrofuran-3-carboxylate (0.15 g, 0.50 mmol) which similarly prepared according to the procedure described in the Example 4, First step and 7-azaindole-3-carboxaldehyde (0.072 g, 0.50 mmol) in ethanol (6.0 mL), L-proline (0.0060 g, 0.05 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 (0.060 g, y. 28%).

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-059295f5a2484757861f6332d1ccb7a4
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

Loading…