1,1'-Carbonyldiimidazole → HCID 20132392, Verbindung

HRID 845245

Reaktionsgleichung

[CH3:1][O:2][CH2:3][C:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[NH:9][C:8]=2[CH:7]=[N:6][C:5]=1[C:24](O)=[O:25].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:39](=[N:43]O)([NH2:42])[CH2:40][CH3:41]>CN(C)C=O>[CH3:1][O:2][CH2:3][C:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[NH:9][C:8]=2[CH:7]=[N:6][C:5]=1[C:24]1[O:25][N:43]=[C:39]([CH2:40][CH3:41])[N:42]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A solution of 0.36 g of 4-methoxymethyl-5-morpholinomethyl-beta-carboline-3-carboxylic acid (prepared according to example 4) in 10 ml of absolute dimethylformamide is mixed with 0.2 g of carbonyldiimidazole and stirred for 30 minutes at 60° C. Then 0.4 g of propioamidoxime in 2 ml of DMF is added and the reaction mixture heated to 100° C. for 3 hours. After distilling off of the solvent in a vacuum, the residue is mixed with 20 ml of xylene and refluxed for 3 hours on the water separator, the reaction mixture is filtered hot, the filtrate is concentrated and chromatographed on silica gel. 0.25 g (60%) of oxadiazole derivative is obtained. Melting point 161°-163° C.

Aufarbeitung

temperaturethe reaction mixture heated to 100° C. for 3 hours
distillationAfter distilling off of the solvent in a vacuum
additionthe residue is mixed with 20 ml of xylene
temperaturerefluxed for 3 hours on the water separator
filtrationthe reaction mixture is filtered hot
concentrationthe filtrate is concentrated
customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-844a499bc1f2435293b62aada34c38da
Quelldatensatz: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04757070

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