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Hydrochloric Acid → 3-tert-butyl-1-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-1-methyl-urea

HRID 240678
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Reaktionsgleichung

Reaktionsgleichung von HRID 240678
Cl.[O:2]=[C:3]1[CH:8]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19][NH:20][CH3:21])[C:10]2=[O:22])[CH2:7][CH2:6][C:5](=[O:23])[NH:4]1.[C:24]([N:28]=[C:29]=[O:30])([CH3:27])([CH3:26])[CH3:25].C(N(C(C)C)CC)(C)C.Cl>C(Cl)Cl.O>[C:24]([NH:28][C:29](=[O:30])[N:20]([CH2:19][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[C:17](=[O:18])[N:9]([CH:8]1[CH2:7][CH2:6][C:5](=[O:23])[NH:4][C:3]1=[O:2])[C:10]2=[O:22])[CH3:21])([CH3:27])([CH3:26])[CH3:25]
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 62412tert-Butyl isocyanateHCID 81531DiisopropylethylamineHCID 670266492-(2,6-Dioxo-piperidin-3-yl)-4-methylaminomethyl-isoindole-1,3-dione hydrochloride

Produkt 1

HCID 248958983-tert-butyl-1-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-1-methyl-ureaAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-(2,6-dioxo-piperidin-3-yl)-4-methylaminomethyl-isoindole-1,3-dione hydrochloride (0.65 g, 1.93 mmol) and t-butyl-isocyanate (0.26 mL, 2.31 mmol) in dry CH2Cl2 (80 ml), was added diisopropylethylamine (0.47 mL g, 2.60 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was added water (40 mL) and 1N HCl (40 mL). The mixture was quenched with MeOH and extracted with H2O (40 mL), then with 1N HCl (40 mL). The organic layer was washed with brine (40 mL) and concentrated on rota-vap. The resulting oil was purified on silica gel column to give 3-tert-butyl-1-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-1-methyl-urea (0.59 g, 76%): mp 188-190° C.; HPLC: Waters Symmetry C-18, 3.9×150 mm, 5 micro, 1 mL/min, 240 nm, 40/60 (CH3CN/H2O): tR=3.14 (96%); 1H NMR (DMSO-d6): δ 1.28 (s, 9H), 2.08 (m, 1H), 2.64-2.50 (m, 2H), 2.85 (s, 3H), 2.87-2.95 (m, 1H), 4.87 (s, 2H), 5.14-5.18 (dd, J=5.3, 12.6 Hz, 1H), 5.71 (s, 1H), 7.50-7.52 (m, 1H), 7.79-7.88 (m, 2H), 11.13 (s, 1H). 13C NMR (DMSO-d6) δ: 21.95, 29.13, 30.90, 34.81, 47.02, 48.82, 50.07, 121.70, 127.45, 131.73, 132.49, 134.78, 139.63, 157.40, 166.95, 167.61, 169.80, 172.73. Anal Calcd for C20H24N4O5: C, 59.99; H, 6.04; N, 13.99. Found: C, 59.87; H, 6.01; N, 13.83.

Aufarbeitung

  1. customThe mixture was quenched with MeOH
  2. extractionextracted with H2O (40 mL)
  3. washThe organic layer was washed with brine (40 mL)
  4. concentrationconcentrated on rota-vap
  5. customThe resulting oil was purified on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-7c9a9b45b7624086a7654b9aae4cfd00
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08648096B2

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