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HRID 2103519Erstellt: 25. Oktober 2026

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

https://huagongshe.com/reaction/2103519

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 10132095—

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 mL0 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
PatentnummerUS07576104B2
Quelldatensatzuspto-grants-2009_08
ORD IDord-2337887e04dc4d49bc5245c65c63344b
Quellennotizuspto-grants-2009_08