Potassium Carbonate → tert-butyl 2-(4-(N-(2-morpholinoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate

HRID 571289Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8](=[O:24])[N:9]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]2=[O:15])(=[O:4])=[O:3].Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[O:32]1[CH2:33][CH2:34][N:29]([CH2:28][CH2:27][N:5]([C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[C:8](=[O:24])[N:9]([CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:10]3=[O:15])[S:2]([CH3:1])(=[O:3])=[O:4])[CH2:30][CH2:31]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of tert-butyl 2-(4-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (196 mg, 0.553 mmol) (prepared with an analogous procedure to that described in, Example 29, Scheme 29, Steps 1, 2, 3, 4 for the preparation of Compound 160), 4-(2-chloroethyl)morpholine hydrochloride (108 mg, 0.581 mmol), and K2CO3 (168 mg, 1.217 mmol) in acetonitrile (10 ml) was stirred at 75° C. overnight. The solvent was removed under vacuum, and the residue was taken up in a EtOAc/DCM/Et2O mixture and filtered through Na2SO4 to remove the inorganic salts. After evaporation of the solvent, tert-butyl 2-(4-(N-(2-morpholinoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate was obtained (256 mg, 0.548 mmol, 99% yield, MS/ESI+ 467 [MH]+).

Workup

customprepared with an analogous procedure to
customThe solvent was removed under vacuum
filtrationfiltered through Na2SO4
customto remove the inorganic salts
customAfter evaporation of the solvent

Sources & evidence

ORD record: ord-f96ea8ea11ee47bf9e2088861a446c36
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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