Piperidine → HCID 71278863, compound

HRID 1749797Notes

Reaction equation

HRID 1749797 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][N:27]=2)[C:22]([CH:29]=O)=[CH:21]1.N1CCCCC1>CO>[NH:20]1[C:28]2=[N:27][CH:26]=[CH:25][CH:24]=[C:23]2[C:22](/[CH:29]=[C:7]2\[O:8][C:4]3[C:3]([CH2:12][N:13]4[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]4)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=3[C:6]\2=[O:9])=[CH:21]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 71278947HCID 71278947, compound

Product 1

HCID 71278863HCID 71278863, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 6-hydroxy-7-[(4-methylpiperazin-1-yl)methyl]benzofuran-3(2H)-one (0.100 g, 0.381 mmol) obtained in Example A31, Step 1 in methanol (1.5 mL) was added with 7-aza-1H-indole-3-carboxaldehyde (0.0557 g, 0.381 mmol) and piperidine (0.00324 g, 0.0381 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and then the precipitated solid was collected by filtration to obtain (Z)-2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)-6-hydroxy-7-[(4-methylpiperazin-1-yl)methyl]benzofuran-3(2H)-one (0.109 g, 73%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-6fcf65825e09484680d015971e4e8b5d
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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