HCID 6918648, compound → HCID 18180046, compound

HRID 2230126Notes

Reaction equation

HRID 2230126 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[S:17][C:16]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:15]=3[C:14]=2[CH3:23])(=[O:12])=[O:11])=[CH:5][C:4]=1[N:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1>ClCCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[S:17][C:16]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:15]=3[C:14]=2[CH3:23])(=[O:12])=[O:11])=[CH:5][C:4]=1[N:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1

Participants

3

Reactant 1

HCID 6918648HCID 6918648, compound

Product 1

HCID 18180046HCID 18180046, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of boron tribromide dimethyl sulphide complex (620 mg, 2 mmol) in 1,2 dichloroethane (30 ml) under argon was added 5-chloro-3-methyl-benzo[b]thiophene-2-sulphonic acid [4-methoxy-3-(4-methyl-piperazin-1-yl)phenyl]amide (E17) (0.2 mmol). The reaction mixture was heated to reflux for 12 hrs, cooled, quenched by the addition of water (20 ml) and partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the title compound (E113). Found MH+ 452/454

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 hrs
  3. temperaturecooled
  4. customquenched by the addition of water (20 ml)
  5. custompartitioned between saturated aqueous sodium bicarbonate and dichloromethane
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9a3b4554da704467b750bebbc9915cfd
Source dataset
uspto-grants-2002_07
Patent number
US06423717B1

Reaction notes

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