L-Proline → HCID 178469600, compound

HRID 402673Notes

Reaction equation

HRID 402673 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[O:16][CH2:17][C:18](=[O:25])[C:19]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:10]([CH3:26])[CH:9]=1.[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][N:34]=2)[C:29]([CH:36]=O)=[CH:28]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:27]1[C:35]2=[N:34][CH:33]=[CH:32][CH:31]=[C:30]2[C:29]([CH:36]=[C:17]2[O:16][C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][OH:1])=[CH:9][C:10]=3[CH3:26])=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]2=[O:25])=[CH:28]1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708372HCID 86708372, compound

Product 1

HCID 178469600HCID 178469600, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-({4-[2-(2-hydroxyethoxy)ethoxy]-2-methylphenyl}amino)-4-oxo-4,5-dihydrofuran-3-carboxylate (0.15 g, 0.50 mmol) which similarly prepared according to the procedure described in the Example 74, First step to Fourth step and 7-azaindole-3-carboxaldehyde (0.070 g, 0.50 mmol) in ethanol (10 mL), L-proline (0.010 g, 0.087 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 diethyl ether then dried to afford the titled compound (0.031 g, y. 15%) as solid.

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 diethyl ether
  5. customthen dried

Sources & evidence

ORD record
ord-b59eadabf5eb4bd389c791e9bba6ce4e
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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