1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10239024, Verbindung

HRID 967824

Reaktionsgleichung

Reaktionsgleichung von HRID 967824
[CH2:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:23](=[O:31])OC3C=CC=CC=3)=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)[CH3:2].[CH3:32][C:33]1[CH:34]=[CH:35][C:36]([S:39]([NH2:42])(=[O:41])=[O:40])=[N:37][CH:38]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH2:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][C:23]([NH:42][S:39]([C:36]3[CH:35]=[CH:34][C:33]([CH3:32])=[CH:38][N:37]=3)(=[O:41])=[O:40])=[O:31])=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 36141995-Methyl-2-pyridinesulfonamideHCID 22291379HCID 22291379, Verbindung

Produkt 1

HCID 10239024HCID 10239024, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of phenyl 2-[4-(2-ethyl-4-phenyl-1H-imidazol-1-yl)phenyl]ethylcarbamate (203 mg, 0.50 mmol), 5-methylpyridine-2-sulfonamide (86 mg, 0.50 mmol) and DBU (82 μL, 0.55 mmol) in acetonitrile (5 mL) was stirred for overnight at ambient temperature. Then, the volatile components were removed by evaporation and the residue was dissolved in dichloromethane. The organic phase was washed with water, dried (MgSO4) and concentrated. The residue was purified by TLC with dichloromethane/methanol (10:1) to afford 145 mg (60%) of the title compound as white solids: MS (ESI) m/z 490 [M+H]+, 488 [M−H]−, 1H-NMR (DMSO-d6) δ 1.18 (3H, t, J=7.5 Hz), 2.37 (3H, s), 2.72-2.90 (4H, m), 3.23 (2H, q, J=6.0 Hz), 6.69 (1H, br), 7.40-7.59 (6H, m), 7.85-7.93 (4H, m), 8.24 (1H, s), 8.55 (1H, s).

Aufarbeitung

  1. customThen, the volatile components were removed by evaporation
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by TLC with dichloromethane/methanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-11124db4cd74422f8dfa75777f7927a4
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956050B2

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