2-Methoxyethylamine → HCID 86681723, compound

HRID 571315Notes

Reaction equation

Br[CH2:2][CH2:3][N:4]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:12]2=[O:30])[S:5]([CH3:8])(=[O:7])=[O:6].C([O-])([O-])=O.[K+].[K+].[CH3:37][O:38][CH2:39][CH2:40][NH2:41]>C(#N)C>[CH3:37][O:38][CH2:39][CH2:40][NH:41][CH2:2][CH2:3][N:4]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[C:14](=[O:18])[N:13]([CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:12]2=[O:30])[S:5]([CH3:8])(=[O:7])=[O:6]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of benzyl 2-(5-(N-(2-bromoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (0.300 g, 0.606 mmol) in acetonitrile (6 ml), K2CO3 (0.126 g, 0.908 mmol) and 2-methoxyethanamine (0.079 ml, 0.908 mmol) were added, and the resulting mixture was heated under MW irradiation for 1 hour at 130° C. The insoluble inorganic salts were filtered off and the filtrate was evaporated to dryness. The crude was purified by flash chromatography on silica gel column (DCM:MeOH=95:5) affording benzyl 2-(5-(N-(2-(2-methoxyethylamino)ethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (0.154 g, 0.315 mmol, 52.0% yield, MS/ESI+ 490.0 [MH]+).

Workup

filtrationThe insoluble inorganic salts were filtered off
customthe filtrate was evaporated to dryness
customThe crude was purified by flash chromatography on silica gel column (DCM:MeOH=95:5)

Sources & evidence

ORD record: ord-43cb1c0dd6b840c5afa3f7060a8dae9e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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