Dimethylformamide → 8-[3-(2-ethoxycarbonylethyl)ureido]-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one

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Reaktionsgleichung

Cl.[NH2:2][C:3]1[CH:19]=[CH:18][C:17]2[C:8]3[NH:9][C:10](=[O:16])[C:11]4[N:12]([CH:13]=[CH:14][N:15]=4)[C:7]=3[CH2:6][C:5]=2[CH:4]=1.CN(C)C=O.[N:25]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:26]=[O:27]>C(N(CC)CC)C>[CH2:33]([O:32][C:30]([CH2:29][CH2:28][NH:25][C:26](=[O:27])[NH:2][C:3]1[CH:19]=[CH:18][C:17]2[C:8]3[NH:9][C:10](=[O:16])[C:11]4[N:12]([CH:13]=[CH:14][N:15]=4)[C:7]=3[CH2:6][C:5]=2[CH:4]=1)=[O:31])[CH3:34]

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

The preparation is carried out as in Example 32 but from 4 g of 8-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one hydrochloride, 86 ml of dimethylformamide, 7.3 ml of triethylamine and 4.42 g of ethyl 3-isocyanatopropionate and the reaction mixture is stirred at a temperature in the region of 20° C. for 90 hours. After evaporation of the dimethylformamide, 300 ml of water are added and the precipitate formed is filtered, washed with water (50 ml) and then with acetone (2×50 ml) and dried at 60° C. under vacuum (1 mm Hg, 0.13 kPa). There are obtained 2.1 g of 8-[3-(2-ethoxycarbonylethyl)ureido]-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4-one in the form of a beige solid melting above 260° C. (Analysis, % calculated C: 59.84, H: 5.02, N: 18.36, O: 16.78, % found C: 59.5, H: 5.1, N: 18.5).

Aufarbeitung

customAfter evaporation of the dimethylformamide, 300 ml of water
additionare added
customthe precipitate formed
filtrationis filtered
washwashed with water (50 ml)
dry with materialwith acetone (2×50 ml) and dried at 60° C. under vacuum (1 mm Hg, 0.13 kPa)

Quellen und Nachweise

ORD-Eintrag: ord-ceffdc9e48564602abe76da06e327318
Quelldatensatz: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05789406

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