Potassium Carbonate → HCID 86681715, compound

HRID 571307Notes

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][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]2=[O:27])[S:5]([CH3:8])(=[O:7])=[O:6].C([O-])([O-])=O.[K+].[K+].[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C(#N)C>[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([CH2:2][CH2:3][N:4]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[N:13]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]3=[O:27])[S:5]([CH3:8])(=[O:7])=[O:6])[CH2:37][CH2:36]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of tert-butyl 2-(5-(N-(2-bromoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (300 mg, 0.650 mmol) in acetonitrile (15 ml), K2CO3 (135 mg, 0.975 mmol) and 1-methylpiperazine (0.080 ml, 0.715 mmol) were added, and the resulting mixture was heated under MW irradiation at 130° C. for 1 hour. Additional K2CO3 (44.8 mg, 0.325 mmol) and 1-methylpiperazine (0.036 ml, 0.325 mmol) were added, and the reaction was submitted to a second microwave cycle at 130° C. for 1 hour. The mixture was diluted with acetonitrile, the insoluble inorganic salts were filtered off, and the filtrate was evaporated under vacuum. Purification by flash chromatography (DCM/MeOH 95/5) afforded tert-butyl 2-(5-(N-(2-(4-methylpiperazin-1-yl)ethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (149 mg, 0.310 mmol, 47.7% yield, MS/ESI+ 480.9 [MH]+).

Workup

filtrationthe insoluble inorganic salts were filtered off
customthe filtrate was evaporated under vacuum
customPurification by flash chromatography (DCM/MeOH 95/5)

Sources & evidence

ORD record: ord-75bd07b0904f42fea411aebc9e048a92
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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