Thioglycolic Acid → 1,3,3,5-Tetramethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 2196077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196077
[OH-].[Li+].C(O)(=O)CS.[N+](C1C=CC=CC=1S([N:20]([CH2:42][CH2:43][C:44]1[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=1)[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:41]=[CH:40][C:28]2[N:29]([CH3:39])[C:30](=[O:38])[C:31]([CH3:37])([CH3:36])[C:32](=[O:35])[N:33]([CH3:34])[C:27]=2[CH:26]=1)(=O)=O)([O-])=O>CN(C=O)C>[CH3:39][N:29]1[C:30](=[O:38])[C:31]([CH3:37])([CH3:36])[C:32](=[O:35])[N:33]([CH3:34])[C:27]2[CH:26]=[C:25]([O:24][CH2:23][CH2:22][CH2:21][NH:20][CH2:42][CH2:43][C:44]3[CH:45]=[N:46][CH:47]=[CH:48][CH:49]=3)[CH:41]=[CH:40][C:28]1=2

Komponenten

5

Edukt 3

HCID 1133Thioglycolic AcidHCID 3939Lithium HydroxideHCID 686742442-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1,3,3,5-tetramethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamide

Produkt 1

HCID 686728731,3,3,5-Tetramethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Lithium hydroxide (0.36 g, 15 mmol) and thioglycolic acid (0.48 ml, 6.9 mmol) were added to a DMF solution (20 ml) of 2-nitro-N-(2-pyridin-3-ylethyl)-N-[3-(1,3,3,5-tetramethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-yloxy)propyl]benzenesulfonamide (2.05 g, 3.4 mmol), and stirred at room temperature for 3 days. The reaction mixture was added to ice water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→dichloromethane:methanol=10:1→4:1). The purified product was concentrated under reduced pressure to thereby obtain 1.13 g (yield: 81%) of 1,3,3,5-tetramethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→dichloromethane:methanol=10:1→4:1)
  6. concentrationThe purified product was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6c9ca923a2304232ad32a0b74f45a126
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338406B2

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