Piperidine → HCID 178476469, compound

HRID 402681Notes

Reaction equation

HRID 402681 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:5]=[CH:4][C:3]=1[NH:16][C:17]1[O:18][CH2:19][C:20](=[O:25])[C:21]=1[C:22]([O-:24])=[O:23].[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][N:33]=2)[C:28]([CH:35]=O)=[CH:27]1.N1CCC[CH2:39][CH2:38]1>C(O)C>[C:22]([OH:24])(=[O:23])[CH3:21].[NH:26]1[C:34]2=[N:33][CH:32]=[CH:31][CH:30]=[C:29]2[C:28]([CH:35]=[C:19]2[O:18][C:17]([NH:16][C:3]3[CH:4]=[CH:5][C:6]([NH:8][CH2:9][CH2:10][N:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)=[CH:7][C:2]=3[CH3:1])=[C:21]([C:22]([O:24][CH2:38][CH3:39])=[O:23])[C:20]2=[O:25])=[CH:27]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 86708385HCID 86708385, compound

Product 1

HCID 178476469HCID 178476469, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[(2-methyl-4-{[2-(pyrrolidino)ethyl]amino}phenyl)amino]-4-oxo-4,5-dihydrofuran-3-carboxylate (0.32 g, 0.85 mmol) which similarly prepared according to the procedure described in the Example 125, First step to Third step and 7-azaindole-3-carboxaldehyde (0.13 g, 0.85 mmol) in ethanol (5.0 mL), piperidine (0.10 mL, 1.0 mmol) was added at ambient temperature. The mixture was refluxed for 24 h. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC (aqueous ammonium acetate/acetonitrile) to afford the titled compound as solid (0.010 g, y. 3%).

Workup

  1. additionwas added at ambient temperature
  2. temperatureThe mixture was refluxed for 24 h
  3. customthe reaction mixture was purified by preparative HPLC (aqueous ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-8395c02acf9e4c07be83deb322e928c7
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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