Potassium Carbonate → HCID 86681702, compound

HRID 571296Notes

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of tert-butyl 2-(5-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (prepared in an analogous manner as previously described in Example 34, Scheme 34, Steps 1, 2, 3) (400 mg, 1.129 mmol) in acetonitrile (10 ml), potassium carbonate (312 mg, 2.257 mmol), and 1-(2-chloroethyl)piperidine hydrochloride (249 mg, 1.354 mmol) were added. The reaction was heated at 90° C. under microwave irradiation for 2 hours. The solid inorganic salts were filtered off and the filtrate was evaporated to dryness. The resulting crude was crystallized from EtOH affording tert-butyl 2-(1,3-dioxo-5-(N-(2-(piperidin-1-yl)ethyl)methylsulfonamido)isoindolin-2-yl)acetate (450 mg, 0.967 mmol, 86% yield, MS/ESI+ 465.9 [MH]+).

Workup

filtrationThe solid inorganic salts were filtered off
customthe filtrate was evaporated to dryness
customThe resulting crude was crystallized from EtOH

Sources & evidence

ORD record: ord-db5cbe1ea3d14dd79bdd39f7ef45c9b3
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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