L-Proline → HCID 178469997, compound

HRID 402706Notes

Reaction equation

HRID 402706 reaction equation
[CH3:1][N:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:3][C:4]1[O:5][CH2:6][C:7](=[O:14])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[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:3][N:2]([CH3:1])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:7]2=[O:14])=[CH:22]1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708401HCID 86708401, compound

Product 1

HCID 178469997HCID 178469997, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(2-methyl-2-phenylhydrazinyl)-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.36 mmol) which similarly prepared according to the procedure described in the Example 74, Fourth step and 7-azaindole-3-carboxaldehyde (0.053 g, 0.36 mmol) in ethanol (10 mL), L-proline (0.020 g, 0.17 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 hexane then dried to afford the titled compound as solid (0.015 g, y. 10%).

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 hexane
  5. customthen dried

Sources & evidence

ORD record
ord-9dab03b3e63d48019d6c0ee1b5b9ae54
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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