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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 906755Erstellt: 25. Oktober 2026

Methanol → N-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)cyclopropanecarboxamide

https://huagongshe.com/reaction/906755

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktMethanolHCID 887—
EduktCyclopropanecarbonyl chlorideHCID 77637—
EduktPomalidomideHCID 134780—
LösungsmittelDiethyl EtherHCID 3283—
LösungsmittelTetrahydrofuranHCID 8028—
ProduktN-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)cyclopropanecarboxamideHCID 1013209584%

Reaktionsschritte

A mixture of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.60 g, 2.2 mmol) and cyclopropanecarbonyl chloride (0.4 mL, 4.4 mmol) in THF (20 mL) was heated to reflux for 15 h. To the mixture was added methanol (5 mL). The solvent was removed in vacuo to give a solid. The solid was slurried in ether (30 mL) for 1 h. The suspension was filtered and washed with ether (30 mL) to give cyclopropanecarboxylic acid [2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-amide as a solid (630 mg, 84% yield): mp, 237-239° C.; 1H NMR (DMSO-d6) δ 0.87-0.90 (m, 4H, 2CH2), 1.93-2.09 (m, 2H, CH, CHH), 2.49-2.65 (m, 2H, CH2), 2.64-2.96 (m, 1H, CHH), 5.15 (dd, J=5.2, 12.6 Hz, 1H, NCH), 7.61 (d, J=7.2 Hz, 1H, Ar), 7.82 (t, J=7.7 Hz, 1H, Ar), 8.41 (d, J=8.3 Hz, 1H, Ar), 9.99 (s, 1H, NH), 11.16 (s, 1H, NH); 13C NMR (DMSO-d6) δ 8.10, 14.93, 22.00, 30.93, 48.92, 117.07, 118.30, 126.69, 131.49, 135.97, 136.43, 166.67, 167.57, 169.77, 172.55, 172.74; Anal Calcd for C17H15N3O5: C, 59.82; H. 4.43; N. 12.31. Found: C, 59.50; H, 4.39; N, 12.04.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08012997B2
Quelldatensatzuspto-grants-2011_09
ORD IDord-8f2da509c7924fb4a5bf040c8ebcc6c6
Quellennotizuspto-grants-2011_09