Dimethyl Sulfoxide → 3-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridine-2-carbaldehyde

HRID 68980

Reaktionsgleichung

Reaktionsgleichung von HRID 68980
I(C1C=CC=CC=1C(O)=O)(=O)=O.CS(C)=O.[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([CH2:35][N:36]([CH2:50][C:51]3[C:52]([CH2:57][OH:58])=[N:53][CH:54]=[CH:55][CH:56]=3)[CH2:37][CH2:38][N:39]3[CH:44]=[CH:43][C:42]4[O:45][C:46]([CH3:48])=[CH:47][C:41]=4[C:40]3=[O:49])[CH:33]=[CH:34][C:20]1=2)[CH3:18]>O>[CH2:17]([N:19]1[C:25](=[O:26])[C:24]([CH3:28])([CH3:27])[C:23](=[O:29])[N:22]([CH3:30])[C:21]2[CH:31]=[C:32]([CH2:35][N:36]([CH2:50][C:51]3[C:52]([CH:57]=[O:58])=[N:53][CH:54]=[CH:55][CH:56]=3)[CH2:37][CH2:38][N:39]3[CH:44]=[CH:43][C:42]4[O:45][C:46]([CH3:48])=[CH:47][C:41]=4[C:40]3=[O:49])[CH:33]=[CH:34][C:20]1=2)[CH3:18]

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 1087942-Iodoxybenzoic acidHCID 669612451-Ethyl-7-({N-(2-hydroxymethylpyridin-3-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Produkt 1

HCID 888768503-({N-(1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-[2-(2-methyl-4-oxo-4H-furo[3,2-c]pyridin-5-yl)ethyl]amino}methyl)pyridine-2-carbaldehydeAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2-iodoxybenzoic acid (IBX, 0.235 g) was added to the dimethyl sulfoxide suspension (10 mL) of 1-ethyl-7-((N-((2-(hydroxymethyl)pyridin-3-yl)methyl)-N-(2-(2-methyl-4-oxofuro[3,2-c]pyridin-5(4H)-yl)ethyl)amino)methyl)-3,3,5-trimethyl-1H-benzo[b][1,4]diazepine-2,4(3H, 5H)-dione (0.48 g) and the mixture was stirred overnight at room temperature. Water was added to the resulting mixture and then the mixture was extracted with ethyl acetate twice. The combined organic layer was concentrated under reduced pressure, and then the residue was purified by column-chromatography (ethyl acetate:hexanes=50:50→100:0). The purified product was recrystallized from ether to afford the titled compound as ivory powder (0.29 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. concentrationThe combined organic layer was concentrated under reduced pressure
  3. customthe residue was purified by column-chromatography (ethyl acetate:hexanes=50:50→100:0)
  4. customThe purified product was recrystallized from ether

Quellen und Nachweise

ORD-Eintrag
ord-b3e399c4d7394693a006696ab522c08e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822453B2

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