Tetrahydrofuran → 6-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1,4-dihydro-quinoxaline-2,3-dione

HRID 642883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642883
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:28]=[C:29]([NH2:34])[C:30]([NH2:33])=[CH:31][CH:32]=5)[CH2:22][CH2:21]4)[C:13]=3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[C:40](N1C=CN=C1)(=[O:48])[C:41](N1C=CN=C1)=[O:42]>C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:21][CH2:22][N:23]([CH2:26][C:27]5[CH:28]=[C:29]6[C:30](=[CH:31][CH:32]=5)[NH:33][C:41](=[O:42])[C:40](=[O:48])[NH:34]6)[CH2:24][CH2:25]4)[C:13]=3[N:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 1004391,1'-OxalyldiimidazoleHCID 58592820HCID 58592820, Verbindung

Produkt 1

HCID 445934246-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1,4-dihydro-quinoxaline-2,3-dioneAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a round bottom flask under nitrogen was combined 4-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-benzene-1,2-diamine (0.17 g, 0.37 mMol), tetrahydrofuran (20 mL), and 1,1′-oxalyldiimidazole (0.284 g, 1.5 mMol) and the solution stirred overnight. Upon arrival the solution was diluted with ethyl acetate (100 mL) and washed with water (100 mL). A precipitate forms and was collected by filtration. The organic layer was concentrated to dryness on a rotary evaporator and combined with the precipitate. Purification by RP-HPLC (Method E) yielded 46 mg (24% yield) of 6-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1,4-dihydro-quinoxaline-2,3-dione as an off-white solid. 1H NMR (DMSO-d6): δ=12.19 (s, 1H), 12.09 (s, 1H), 9.82 (br s, 1H), 8.07 (d, 2H, J=8.6 Hz), 7.58 (d, 2H, J=8.6 Hz), 7.27 (m, 2H), 7.22 (d ,1H, J=8.6 Hz), 7.13 (m, 2H), 6.64 (m, 1H), 4.48 (br s, 2H), 4.44 (s, 2H), 3.50 (br s, 2H), 3.38 (br s, 2H), 3.09 (m, 2H), 1.34 (s, 9H). HPLC: Xterra MS C18, 3.5 μm, 4.6×50 mm, flow=0.8 m/min, 5-95% ACN/PICB6 over 10 mins., rt=5.840 mins., 79% pure @ 210 nm, 77% pure @ 300 nm. LC/MS (Method A), rt=1.05 mins., purity=79.19%, calculated mass=508, [M+H]+=509, [M−H]−=507.

Aufarbeitung

  1. customIn a round bottom flask under nitrogen was combined
  2. washwashed with water (100 mL)
  3. filtrationA precipitate forms and was collected by filtration
  4. concentrationThe organic layer was concentrated to dryness on a rotary evaporator
  5. customPurification by RP-HPLC (Method E)

Quellen und Nachweise

ORD-Eintrag
ord-8606f4d0ecd745adb48a1063849204b9
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696210B2

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