Dimethylformamide → 2-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamide

HRID 1183098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183098
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH:24][CH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)(=[O:23])=[O:22])([O-:14])=[O:13].[CH2:33]([N:35]1[C:41](=[O:42])[C:40]([CH3:44])([CH3:43])[C:39](=[O:45])[N:38]([CH3:46])[C:37]2[CH:47]=[C:48]([O:51][CH2:52][CH2:53][CH2:54]I)[CH:49]=[CH:50][C:36]1=2)[CH3:34]>C(OCC)(=O)C.O>[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]([CH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH2:54][CH2:53][CH2:52][O:51][C:48]1[CH:49]=[CH:50][C:36]2[N:35]([CH2:33][CH3:34])[C:41](=[O:42])[C:40]([CH3:44])([CH3:43])[C:39](=[O:45])[N:38]([CH3:46])[C:37]=2[CH:47]=1)(=[O:22])=[O:23])([O-:14])=[O:13]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 465565342-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamideHCID 686727921-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Produkt 1

HCID 686735912-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamideAusbeute 107,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium carbonate (1.89 g, 13.7 mmol) was added to a DMF solution (50 ml) of 2-nitro-N-(2-pyridin-3-ylethyl)benzene sulfonamide (1.40 g, 4.56 mmol) and 1-ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4 ]diazepine-2,4-dione (2.16 g, 5.0 mmol), and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with water and a saturated sodium chloride aqueous solution in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1). The purified product was concentrated under reduced pressure to thereby obtain 2.99 g (yield: quantitative) of 2-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamide as a yellow oil.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. dry with materiala saturated sodium chloride aqueous solution in this order, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=1:0→10:1)
  5. concentrationThe purified product was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-faa6aced635944ebaee375a64cfc7fab
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664217B2

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