Dimethylformamide → (R)-N'-(8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-7-carbothioyl)-acetic hydrazide

HRID 25074

Reaktionsgleichung

[CH3:1][C@@H:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25](Cl)=[S:26].CN(C)C=O.C(N(CC)CC)C.[C:40]([NH:43][NH2:44])(=[O:42])[CH3:41]>CN(C)C1C=CN=CC=1.O>[CH3:1][C@@H:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25]([NH:44][NH:43][C:40](=[O:42])[CH3:41])=[S:26]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 4.04 g (10.0 mmol) of the starting material XII, 3 ml of dimethylformamide, 1.40 ml (10.0 mmol) of triethylamine and 0.06 g (0.5 mmol) of 4-dimethylaminopyridine 1.48 g (20.0 mmol) of acetic hydrazide was added. The reaction mixture was stirred at 50° C. for 5 h, then diluted with water, the precipitated crystals were filtered off and washed with water. The so obtained 4.5 g of (R)—N′-{8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbothioyl}-acetic hydrazide according to its 1H-NMR spectrum was a mixture of rotation isomers. (The analyzed sample was purified by column chromatography using a mixture of n-hexane-ethyl acetate (1:1) as eluent and it was crystallized with 0.5 mol of ethyl acetate, Mp.: 118° C.).

Aufarbeitung

filtrationthe precipitated crystals were filtered off
washwashed with water

Quellen und Nachweise

ORD-Eintrag: ord-aca65a8d2fc7443881e36f7679c978c1
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06858605B2

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