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9-(4,5-dihydrofuran-2-yl)-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one → 2-(4-ethyl-1H-imidazol-1-yl)-9-(tetrahydrofuran-2-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

HRID 926322
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 926322
[O:1]1[CH2:5][CH2:4][CH:3]=[C:2]1[C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][N:10]1[C:20](=[O:21])[CH2:19][N:18]=[C:17]([N:22]3[CH:26]=[C:25]([CH2:27][CH3:28])[N:24]=[CH:23]3)[CH:16]=[C:11]12>C1COCC1.[Ni]>[CH2:27]([C:25]1[N:24]=[CH:23][N:22]([C:17]2[CH:16]=[C:11]3[C:12]4[C:7]([CH2:8][CH2:9][N:10]3[C:20](=[O:21])[CH2:19][N:18]=2)=[C:6]([CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[CH:15]=[CH:14][CH:13]=4)[CH:26]=1)[CH3:28]
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Komponenten

4

Edukt 1

HCID 867113929-(4,5-dihydrofuran-2-yl)-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

Produkt 1

HCID 733360192-(4-ethyl-1H-imidazol-1-yl)-9-(tetrahydrofuran-2-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-oneAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Example 111. A flask was charged with 9-(4,5-dihydrofuran-2-yl)-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (250 mg, 0.67 mmol) in 20 mL THF and Raney-Nickel (100 mg, 0.67 mmol) was added. The flask was evacuated in vacuo and then filled with H2. The mixture was stirred at RT for 36 h. The reaction mixture was then filtered and the filtrate concentrated in vacuo. The residue obtained was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1) and the product obtained was recrystallized from heptane to give the title compound (63 mg; racemic) as beige solid. UPLC-MS: MS 377.3 (M+H+); UPLC rt 0.83 min. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.13 (t, J=7.62 Hz, 3H); 1.47-1.64 (m, 1 H); 1.81-2.00 (m, 2 H); 2.24-2.40 (m, 1 H); 2.40-2.55 (m, 2 H); 2.74-3.04 (m, 2 H); 3.59-3.74 (m, 1 H); 3.81 (q, J=7.56 Hz, 1 H); 3.86-3.97 (m, 1 H); 4.03 (q, J=7.17 Hz, 1 H); 4.21 (br. s., 2 H); 5.04 (t, J=7.04 Hz, 1 H); 7.06-7.17 (m, 1 H); 7.25-7.44 (m, 2 H); 7.52 (d, J=7.43 Hz, 1 H); 7.89 (d, J=8.21 Hz, 1 H); 8.12 (s, 1 H).

Aufarbeitung

  1. additionwas added
  2. customThe flask was evacuated in vacuo
  3. additionfilled with H2
  4. filtrationThe reaction mixture was then filtered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue obtained
  7. customwas purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1)
  8. customthe product obtained
  9. customwas recrystallized from heptane

Quellen und Nachweise

ORD-Eintrag
ord-578d831738b9405e97f633887a40b9df
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09284331B2

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