L-Proline → HCID 178469587, compound

HRID 402677Notes

Reaction equation

HRID 402677 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[NH:16][C:17]1[O:18][CH2:19][C:20](=[O:27])[C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][N:35]=2)[C:30]([CH:37]=O)=[CH:29]1.N1CCC[C@H]1C(O)=O>C(O)C>[NH:28]1[C:36]2=[N:35][CH:34]=[CH:33][CH:32]=[C:31]2[C:30]([CH:37]=[C:19]2[O:18][C:17]([NH:16][C:3]3[CH:4]=[CH:5][C:6]([O:8][CH2:9][C:10]4[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=4)=[CH:7][C:2]=3[CH3:1])=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:20]2=[O:27])=[CH:29]1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708383HCID 86708383, compound

Product 1

HCID 178469587HCID 178469587, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-{[2-methyl-4-(3-pyridinylmethoxy)phenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate (0.080 g, 0.20 mmol) which similarly prepared according to the procedure described in the Example 74, First step to Fourth step and 7-azaindole-3-carboxaldehyde (0.032 g, 0.20 mmol) in ethanol (5.0 mL), L-proline (0.0050 g, 0.043 mmol) was added at ambient temperature. The mixture was refluxed for 2 days. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.010 g, y. 9%).

Workup

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

Sources & evidence

ORD record
ord-426bd73567ad42a08bf3fd884fce1dd5
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

Loading…