Piperidine → HCID 178469544, compound

HRID 402674Notes

Reaction equation

HRID 402674 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][C:3]=1[NH:14][C:15]1[O:16][CH2:17][C:18](=[O:23])[C:19]=1[C:20]([O-:22])=[O:21].[NH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][N:31]=2)[C:26]([CH:33]=O)=[CH:25]1.N1CCC[CH2:37][CH2:36]1>C(O)C>[NH:24]1[C:32]2=[N:31][CH:30]=[CH:29][CH:28]=[C:27]2[C:26]([CH:33]=[C:17]2[O:16][C:15]([NH:14][C:3]3[CH:4]=[CH:5][C:6]([CH2:8][N:9]4[CH2:13][CH2:12][CH2:11][CH2:10]4)=[CH:7][C:2]=3[CH3:1])=[C:19]([C:20]([O:22][CH2:36][CH3:37])=[O:21])[C:18]2=[O:23])=[CH:25]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708374HCID 86708374, compound

Product 1

HCID 178469544HCID 178469544, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-{[2-methyl-4-(1-pyrrolidinylmethyl)phenyl]amino}-4-oxo-4,5-dihydrofuran-3-carboxylate (0.25 g, 0.70 mmol) which similarly prepared according to the procedure described in the Example 129, First step to Third step and 7-azaindole-3-carboxaldehyde (0.10 g, 0.70 mmol) in ethanol (10 mL), piperidine (0.014 mL, 0.14 mmol) was added at ambient temperature. The mixture was refluxed for 2 days. Cooled to ambient temperature then the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.035 g, y. 10%).

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-fd4367a527964d6e94a323e690c8357b
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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