Potassium Carbonate → HCID 86681757, compound

HRID 571340Notes

Reaction equation

HRID 571340 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C([O-])([O-])=O.[K+].[K+].[CH3:17][S:18]([NH:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[N:27]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:26]2=[O:41])(=[O:20])=[O:19]>CN(C=O)C>[O:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][N:21]([CH2:22][C:23]2[CH:24]=[C:25]3[C:29](=[CH:30][CH:31]=2)[C:28](=[O:32])[N:27]([CH2:33][C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[C:26]3=[O:41])[S:18]([CH3:17])(=[O:19])=[O:20])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 86681754HCID 86681754, compound

Product 1

HCID 86681757HCID 86681757, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(2-chloroethyl)morpholine hydrochloride (0.195 g, 1.050 mmol), K2CO3 (0.242 g, 1.751 mmol) and tert-butyl 2-(5-(methylsulfonamidomethyl)-1,3-dioxoisoindolin-2-yl)acetate (0.258 g, 0.700 mmol), (prepared in an analogous manner as described in Example 46, Scheme 46, Steps 1, 2, 3, 4), was heated to 80° C. for 5 hours in DMF (10 ml) and then stirred at room temperature overnight. The insoluble inorganic salts were filtered off and then washed with ethyl acetate. The filtrate was concentrated to dryness, and the resulting crude was purified by filtration through a silica gel cartridge (100% DCM to DCM:MeOH=98:2) to afford tert-butyl 2-(5-((N-(2-morpholinoethyl)methylsulfonamido)methyl)-1,3-dioxoisoindolin-2-yl)acetate (0.200 g, 0.415 mmol, 59.3% yield, MS/ESI+ 482.1 [MH]+).

Workup

  1. custom(prepared in an analogous manner
  2. filtrationThe insoluble inorganic salts were filtered off
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated to dryness
  5. filtrationthe resulting crude was purified by filtration through a silica gel cartridge (100% DCM to DCM:MeOH=98:2)

Sources & evidence

ORD record
ord-61dea7ad0788497ab5f44526753397ec
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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