Dicyclohexylcarbodiimide → (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one

HRID 1073707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073707
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.NC1N=CC2C=CC=CC=2N(CCOC2CCCCO2)C1=O.[C:60]1([C:66]2[C:72]3[CH:73]=[CH:74][CH:75]=[CH:76][C:71]=3[N:70]([CH2:77][CH2:78][O:79][CH:80]3[CH2:85][CH2:84][CH2:83][CH2:82][O:81]3)[C:69](=[O:86])[CH:68]([NH2:87])[N:67]=2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>C(Cl)(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:87][CH:68]1[N:67]=[C:66]([C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][C:71]=2[N:70]([CH2:77][CH2:78][O:79][CH:80]2[CH2:85][CH2:84][CH2:83][CH2:82][O:81]2)[C:69]1=[O:86])=[O:12]

Komponenten

7

Edukt 5

HCID 10868DicyclohexylcarbodiimideHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 14800304(3RS)-1,3-dihydro-5-phenyl-3-amino-1-{2-((RS)-2-tetrahydropyranyloxy) ethyl}-2H-1,4-benzodiazepine-2-oneHCID 70360821amino-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one

Produkt 1

HCID 14800305(3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a mixture of indole-2-carboxylic acid (0.19 g), N-hydroxybenzotriazole (0.16 g) and N,N'-dicyclohexylcarbodiimide (0.24 g) in chloroform (10 ml) was added amino-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4- benzodiazepine-2-one and (3RS)-1,3-dihydro-5-phenyl-3-amino-1-{2-((SR) -2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one at ambient temperature under stirring. The mixture was stirred for 2 hours under the same conditions. The resultant precipitate was filtered off. The combined filtrate and washings were evaporated under reduced pressure and the residual oil (1.20 g) was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (10:1) to give a mixture (white powder, 0.45 g) of (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino) -5-phenyl-1-{2-((RS)-2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine-2-one and (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino)-5-phenyl-1-{2-((SR) -2-tetrahydropyranyloxy)ethyl}-2H-1,4-benzodiazepine- 2-one.

Aufarbeitung

  1. stirringThe mixture was stirred for 2 hours under the same conditions
  2. filtrationThe resultant precipitate was filtered off
  3. customThe combined filtrate and washings were evaporated under reduced pressure
  4. additionthe residual oil (1.20 g) was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and ethyl acetate (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-ff40c51532d449bc8529127a5cefbaa3
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04970207

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