Piperidine → (2Z)-6-hydroxy-2-(2H-indazol-3-ylmethylidene)-7-[(4-methylsulfonylpiperazin-1-yl)methyl]-1-benzofuran-3-one

HRID 1749926Notes

Reaction equation

HRID 1749926 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]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH:32]=O)=[N:24]1.N1CCCCC1>CO>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](/[CH:32]=[C:7]2\[O:8][C:4]3[C:3]([CH2:12][N:13]4[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]4)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=3[C:6]\2=[O:9])=[N:24]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 71278800HCID 71278800, compoundHCID 178520025HCID 178520025, compound

Product 1

HCID 178504957(2Z)-6-hydroxy-2-(2H-indazol-3-ylmethylidene)-7-[(4-methylsulfonylpiperazin-1-yl)methyl]-1-benzofuran-3-oneYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of 6-hydroxy-7-{[4-(methylsulfonyl)piperazin-1-yl]methyl}benzofuran-3(2H)-one (0.0681 g, 0.209 mmol) in methanol (0.8 mL) was added with 1H-indazole-3-carboxaldehyde (0.0305 g, 0.209 mmol) and piperidine (0.00178 g, 0.0209 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and then added with methanol (2 mL), and the precipitated solid was suspended in methanol and thereby washed to obtain (Z)-2-[(1H-indazol-3-yl)methylene]-6-hydroxy-7-{[4-(methylsulfonyl)piperazin-1-yl]methyl}benzofuran-3(2H)-one (0.0503 g, 53%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed

Sources & evidence

ORD record
ord-55a8ebbf4853469ead8bd3f8b44e5609
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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