L-Proline → HCID 178469754, compound

HRID 402662Notes

Reaction equation

HRID 402662 reaction equation
[O:1]=[C:2]1[CH2:6][O:5][C:4]([NH:7][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])=[C:3]1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][N:28]=2)[C:23]([CH:30]=O)=[CH:22]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:21]1[C:29]2=[N:28][CH:27]=[CH:26][CH:25]=[C:24]2[C:23]([CH:30]=[C:6]2[O:5][C:4]([NH:7][CH:8]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH3:9])=[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:2]2=[O:1])=[CH:22]1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708355HCID 86708355, compound

Product 1

HCID 178469754HCID 178469754, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-oxo-2-[(1-phenylethyl)amino]-4,5-dihydrofuran-3-carboxylate (0.40 g, 1.5 mmol) which similarly prepared according to the procedure described in the Example 4, First step and 7-azaindole-3-carboxaldehyde (0.21 g, 1.5 mmol) in ethanol (20 mL), L-proline (0.017 g, 0.15 mmol) was added at ambient temperature. The mixture was refluxed for 3 days. Cooled to ambient temperature, the precipitate was collected by filtration, washed with methanol then dried to afford the titled compound as solid (0.20 g, y. 34%).

Workup

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

Sources & evidence

ORD record
ord-6ed77b75ec0b420e8d1728dfbe7ac19b
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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