5-Isocyanato-1,3-dioxaindane → 1-(1,3-benzodioxol-5-yl)-3-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}urea

HRID 18130

Reaktionsgleichung

[NH2:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:9]4[C:14]=2[C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[C:11](=[O:22])[C:10]=4[CH:23]=[CH:24][CH:25]=3)[CH:5]=[CH:4][CH:3]=1.[CH2:26]1[O:34][C:33]2[CH:32]=[CH:31][C:30]([N:35]=[C:36]=[O:37])=[CH:29][C:28]=2[O:27]1.C(Cl)Cl.CO>C(#N)C>[O:34]1[C:33]2[CH:32]=[CH:31][C:30]([NH:35][C:36]([NH:1][C:2]3[C:15]4[C:6](=[CH:7][C:8]5[C:9]6[C:14]=4[C:13](=[O:16])[N:12]([CH2:17][CH2:18][N:19]([CH3:20])[CH3:21])[C:11](=[O:22])[C:10]=6[CH:23]=[CH:24][CH:25]=5)[CH:5]=[CH:4][CH:3]=3)=[O:37])=[CH:29][C:28]=2[O:27][CH2:26]1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

A solution of 100 mg (0.30 mmole) of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) in 4 mL of acetonitrile was stirred at 20° C. 3,4-(methylenedioxy)phenyl isocyanate (2 molar equivalents) in 3 mL acetonitrile were added. The mixture was magnetically stirred at 20° C. during 18 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography on silica (eluent: CH2Cl2/methanol in a 95:5 volume ratio) to provide 125 mg (yield: 84%) of the desired product (formula below) as an orange powder.

Aufarbeitung

customThe solvent was then evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-33b947ef146d494bb67149df97edce5c
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07741337B2

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