HCID 71278791, compound → HCID 178480827, compound

HRID 1749924Notes

Reaction equation

HRID 1749924 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[C:5]2[O:9][CH2:8][C:7](=[O:10])[C:6]=2[CH:11]=1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH:29]=O)=[N:21]1>CO.N1CCCCC1>[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](/[CH:29]=[C:8]2\[O:9][C:5]3[C:4]([CH2:12][N:13]4[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]4)=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=3[C:7]\2=[O:10])=[N:21]1

Participants

5

Reactant 2

HCID 71278791HCID 71278791, compoundHCID 178520025HCID 178520025, compound

Product 1

HCID 178480827HCID 178480827, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-chloro-7-[(4-methylpiperazin-1-yl)methyl]benzofuran-3(2H)-one (0.12 g, 0.43 mmol) in methanol (5.0 mL) was added with 1H-indazole-3-carboxaldehyde (0.063 g, 0.43 mmol). Then, the mixture was added with 7 drops of piperidine, and then the mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, and then the residue was purified by silica gel column chromatography (eluted with chloroform/methanol (99:1→90:10)) to obtain (Z)-2-[(1H-indazol-3-yl)methylene]-5-chloro-7-[(4-methylpiperazin-1-yl)methyl]benzofuran-3(2H)-one (0.042 g, 24%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (eluted with chloroform/methanol (99:1→90:10))

Sources & evidence

ORD record
ord-21878bc1840843d6837a75a780cb9c0a
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…