L-Proline → HCID 178469773, compound

HRID 402711Notes

Reaction equation

HRID 402711 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]([C:7]1[O:8][CH2:9][C:10](=[O:17])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:6].[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>[CH:12]([OH:14])=[O:13].[NH:19]1[C:27]2=[N:26][CH:25]=[CH:24][CH:23]=[C:22]2[C:21]([CH:28]=[C:9]2[O:8][C:7]([N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:18])[CH3:6])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]2=[O:17])=[CH:20]1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708405HCID 86708405, compound

Product 1

HCID 178469773HCID 178469773, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-{[2-(dimethylamino)ethyl]-N-methylamino}-4-oxo-4,5-dihydrofuran-3-carboxylate (0.20 g, 0.78 mmol) which similarly prepared according to the procedure described in the Example 74, Fourth step and 7-azaindole-3-carboxaldehyde (0.11 g, 0.78 mmol) in ethanol (6.0 mL), L-proline (0.0093 mg, 0.078 mmol) was added at ambient temperature. The mixture was refluxed for 20 h. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.035 g, y. 12%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 20 h
  3. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-6d1f6aae290041b69ac94321c00b47f7
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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