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Triethylamine → 1-[1-(2-toluoylmethy)-2-oxo-5-(2-pyridylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)urea

HRID 1979390
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1979390
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]1([CH3:63])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][N:56]=3)=[O:54])[CH2:44][CH:43]([NH2:61])[C:42]2=[O:62])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>O1CCCC1>[C:32]1([CH3:63])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][N:56]=3)=[O:54])[CH2:44][CH:43]([NH:61][C:14]([NH:1][C:2]3[CH:12]=[CH:11][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=3)=[O:16])[C:42]2=[O:62])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 21201574HCID 21201574, Verbindung

Produkt 1

HCID 697003921-[1-(2-toluoylmethy)-2-oxo-5-(2-pyridylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-ethoxycarbonylphenyl)ureaAusbeute 123,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Ethyl 3-aminobenzoate (310 mg) was dissolved in tetrahydrofuran (50 ml), triphosgene (187 mg) was added under ice-cooling, triethylamine (161 μl) was added five times every 3 minutes,a solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-(2-pyridylcarbonyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (730 mg) in tetrahydrofuran (23 ml) was added thereto, and the reaction mixture was allowed to come to room temperature, stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, water (50 ml) was added, extracted with methylene chloride. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(chloroform:ethyl acetate=10:1), to thereby obtain 483 mg of the titled compound.

Aufarbeitung

  1. temperaturecooling
  2. customto come to room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water (50 ml)
  4. additionwas added
  5. extractionextracted with methylene chloride
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography(chloroform:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-205c1982e81d48bbb3b0b9e6d61b2fd5
Quelldatensatz
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06239131B1

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