4-Ethylbenzoyl chloride → 4-Ethyl-N-[[2-[(3S)-3-methyl-2,6-dioxopiperidin-3-YL]-1,3-dioxoisoindolin-5-YL]methyl]benzamide

HRID 331549

Reaktionsgleichung

Reaktionsgleichung von HRID 331549
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)[CH3:2].Cl.[NH2:13][CH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([C@@:25]1([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32])[C:18]2=[O:34]>C(#N)C>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:13][CH2:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[C:20](=[O:24])[N:19]([C@@:25]2([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]2=[O:32])[C:18]3=[O:34])=[O:8])=[CH:5][CH:4]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 853684-Ethylbenzoyl chlorideHCID 670196915-aminomethyl-2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-isoindole-1,3-dione hydrochloride

Produkt 1

HCID 247883104-Ethyl-N-[[2-[(3S)-3-methyl-2,6-dioxopiperidin-3-YL]-1,3-dioxoisoindolin-5-YL]methyl]benzamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

TEA (0.44 g, 4.4 mmol) was added to a mixture of 4-ethylbenzoyl chloride (0.34 g, 2.0 mmol) and 5-aminomethyl-2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-isoindole-1,3-dione hydrochloride (0.67 g, 2.0 mmol) in acetonitrile (20 mL). The mixture was stirred at room temperature for 2 hours, and was evaporated under vacuum. The residue was partitioned between water (100 mL) and ethyl acetate (100 mL), and the organic phase was evaporated. The residue was chromatographed on silica gel using ethyl acetate as the mobile phase, providing 0.65 g, in 76% yield. The product was obtained as a white solid; mp 160-162° C.; HPLC, Waters Symmetry C-18, 3.9×150 mm, 5 μm, 1 mL/min, 240 nm, 45/55 CH3CN/0.1% H3PO4, 4.20 (97.47%); 1H NMR (DMSO-d6) δ 1.19 (t, J=7.7 Hz, 3H), 1.89 (s, 3H), 2.02-2.08 (m, 1H), 2.54-2.62 (m, 2H), 2.65-2.78 (m, 3H), 4.61 (d, J=6.0 Hz, 2H), 7.32 (d, J=8.1 Hz, 2H), 7.76-7.84 (m, 5H), 9.14 (t, J=6.0 Hz, 1H), 11.01 (s, 1H); 13C NMR (DMSO-d6) δ 15.4, 21.1, 28.1, 28.6, 29.2, 42.6, 58.8, 121.6, 123.2, 127.4, 127.8, 129.6, 131.4, 131.5, 133.4, 147.6, 147.7, 166.4, 167.8, 167.9, 172.2, 172.3; Anal. Calcd for C24H23N3O5: C, 66.50; H, 5.35; N, 9.69. Found: C, 66.30; H, 5.26; N, 9.56.

Aufarbeitung

  1. customwas evaporated under vacuum
  2. customThe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. customthe organic phase was evaporated
  4. customThe residue was chromatographed on silica gel
  5. customproviding 0.65 g
  6. customThe product was obtained as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-f81747485ba94cb49cd5856de0a73fba
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877780B2

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