Potassium Carbonate → HCID 86681699, compound

HRID 571294Notes

Reaction equation

HRID 571294 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].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>CN(C=O)C>[O:38]1[CH2:39][CH2:40][N:35]([CH2:34][CH2:33][N:5]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[C:11](=[O:15])[N:10]([CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:9]3=[O:24])[S:2]([CH3:1])(=[O:3])=[O:4])[CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 86681698HCID 86681698, compound

Product 1

HCID 86681699HCID 86681699, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (501 mg, 1.414 mmol) in dry DMF (15 ml) maintained under nitrogen atmosphere, K2CO3 (391 mg, 2.83 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (526 mg, 2.83 mmol) were added, and the mixture was stirred at 60° C. for 3 hours. The solid was filtered off, the solvent was evaporated and the resulting crude was purified by filtration on a silica gel cartridge (DCM/MeOH 9/1), obtaining tert-butyl 2-(5-(N-(2-morpholinoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (570 mg, 1.22 mmol, 86% yield, MS/ESI+ 468.2 [MH]+).

Workup

  1. filtrationThe solid was filtered off
  2. customthe solvent was evaporated
  3. filtrationthe resulting crude was purified by filtration on a silica gel cartridge (DCM/MeOH 9/1)

Sources & evidence

ORD record
ord-e1190405aabc4cb2912b94819c2c86cc
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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