Triethylamine → Methanesulfonamide,n-[3-[(4-chloro-2,3-dihydro-7-iodo-1-oxo-1h-isoindol-5-yl)oxy]propyl]-

HRID 21315Notes

Reaction equation

HRID 21315 reaction equation
Cl.[Cl:2][C:3]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:10][C:9]([I:17])=[C:8]2[C:4]=1[CH2:5][NH:6][C:7]2=[O:18].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[Cl:2][C:3]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][NH:16][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:10][C:9]([I:17])=[C:8]2[C:4]=1[CH2:5][NH:6][C:7]2=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 684884094-Chloro-5-(3-aminopropoxy)-7-iodoisoindolinone hydrochloride

Product 1

HCID 68492844Methanesulfonamide,n-[3-[(4-chloro-2,3-dihydro-7-iodo-1-oxo-1h-isoindol-5-yl)oxy]propyl]-Yield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-5-(3-aminopropoxy)-7-iodoisoindolinone hydrochloride (100 mg, 0.248 mmol) was suspended in dichloromethane (3.0 mL), and the suspension was added with triethylamine (0.104 mL, 0.744 mmol) and methanesulfonyl chloride (0.029 mL, 0.372 mmol), followed by stirring at room temperature for 13 hours. The solvent was evaporated under reduced pressure, and the residue was purified by slurry using water and acetonitrile to obtain 4-chloro-5-[3-(methanesulfonylamino)propoxy]-7-iodoisoindolinone (51.8 mg, yield 47%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by slurry

Sources & evidence

ORD record
ord-38d0b3e4e8f44f649fd85c9b6ec23f7d
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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