Hydrochloric Acid → HCID 86681703, compound

HRID 571297Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]([CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:9]=2)[C:4](=[O:24])[N:3]1[CH2:25][C:26]([O:28]C(C)(C)C)=[O:27].[ClH:33]>O1CCOCC1>[ClH:33].[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N:11]([CH2:16][CH2:17][N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][CH:9]=2)[C:4](=[O:24])[N:3]1[CH2:25][C:26]([OH:28])=[O:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of tert-butyl 2-(1,3-dioxo-5-(N-(2-(piperidin-1-yl)ethyl)methylsulfonamido)isoindolin-2-yl)acetate (450 mg, 0.967 mmol) in dioxane (7 ml), 4 M HCl in dioxane (2.5 ml, 10.00 mmol) was added. The reaction was heated at 100° C. under microwave irradiation for 4 hours. The volatiles were removed under vacuum and the resulting solid was triturated with Et2O and recovered by filtration affording 2-(1,3-dioxo-5-(N-(2-(piperidin-1-yl)ethyl)methylsulfonamido)isoindolin-2-yl)acetic acid hydrochloride (407 mg, 0.913 mmol, 94% yield, MS/ESI+ 409.8 [MH]+).

Workup

customThe volatiles were removed under vacuum
customthe resulting solid was triturated with Et2O
filtrationrecovered by filtration

Sources & evidence

ORD record: ord-70ab8744ddfa48aeb13caa9b07d3cf38
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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