Potassium Iodide → HCID 86681709, compound

HRID 571302Notes

Reaction equation

HRID 571302 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:9]2=[O:24])(=[O:4])=[O:3].Cl.Cl[CH2:27][CH2:28][N:29]([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:30][N:29]([CH3:31])[CH2:28][CH2:27][N:5]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[N:10]([CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:9]2=[O:24])[S:2]([CH3:1])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 86681698HCID 86681698, compound

Product 1

HCID 86681709HCID 86681709, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (600 mg, 1.693 mmol) (prepared in an analogous manner as previously described in Example 34, Scheme 34, Steps 1, 2, 3) in acetone (20 ml), 2-chloro-N,N-dimethylethanamine hydrochloride (366 mg, 2.54 mmol), potassium carbonate (468 mg, 3.39 mmol) and potassium iodide (281 mg, 1.693 mmol) were added. The resulting mixture was stirred at 50° C. for 48 hours. The insoluble inorganic salts were filtered off, and the filtrate was evaporated. The crude was purified by was crystallization from EtOH affording tert-butyl 2-(5-(N-(2-(dimethylamino)ethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (300 mg, 0.705 mmol, 41.6% yield, MS/ESI+ 426.0 [MH]+).

Workup

  1. filtrationThe insoluble inorganic salts were filtered off
  2. customthe filtrate was evaporated
  3. customThe crude was purified
  4. customcrystallization from EtOH

Sources & evidence

ORD record
ord-e060afaa9f93442ab93c45760df563b8
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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