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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(3-Methylphenyl)urea

HRID 963517
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 963517
OC(CN1C2C=CC=CC=2C(C2C=CC=CC=2F)=NC([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=2)=[O:25])C1=O)=O.Cl.Cl.CN1C2CCC1CNC2.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(N(CC)CC)C>[CH3:33][C:29]1[CH:28]=[C:27]([NH:26][C:24](=[O:25])[NH2:23])[CH:32]=[CH:31][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 19081198N-[(3RS)-1-hydroxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)ureaHCID 221201898-Methyl-3,8-diazabicyclo(3.2.1)octane dihydrochloride

Produkt 1

HCID 6142
N-(3-Methylphenyl)urea
Ausbeute 311,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of N-[(3RS)-1-hydroxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea (0.295 g) and 8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (0.189 g) in N,N-dimethylformamide (10 ml) was added l-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (0.150 g), 1-hydroxy-1H-benzotriazole monohydrate (0.120 g) and a solution of triethylamine (0.255 g) in N,N-dimethylformamide (2 ml). The. mixture was stirred overnight at ambient temperature. Then the mixture was heated at 80° C. for 1 hour. The mixture was concentrated in vacuo. The residue was treated with water, alkalized with sodium carbonate and extracted with chloroform. The extract was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and methanol (50:1) to give N-[(3RS)-5-(2-fluorophenyl)-I-(8-methyl-3,8-diazabicyclo[3.2.1]-oct-3-yl)]carbonylmethyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea (0.300 g) as a colorless crystal.

Aufarbeitung

  1. temperatureThen the mixture was heated at 80° C. for 1 hour
  2. concentrationThe mixture was concentrated in vacuo
  3. additionThe residue was treated with water
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and methanol (50:1)

Quellen und Nachweise

ORD-Eintrag
ord-09b67994194446b9ad034c45b81506b5
Quelldatensatz
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05763437

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