Diisopropylethylamine → 5-Chloro-4-(4-isobutylpiperazin-1-yl)-3-nitropyridin-2-amine

HRID 416750

Reaktionsgleichung

[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([Cl:12])=[CH:4][N:3]=1.[CH2:13]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[CH:14]([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C>C(O)(C)C>[Cl:12][C:5]1[C:6]([N:20]2[CH2:21][CH2:22][N:17]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:18][CH2:19]2)=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[N:3][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

To a mixture of 2-amino-4,5-dichloro-3-nitropyridine (0.060 g, 0.29 mmol) and isopropanol (4.5 ml) was added 1-isobutyl-piperazine (0.045 g, 0.32 mmol) with the aid of isopropanol (0.5 ml) followed by diisopropylethylamine (0.06 ml, 0.32 mmol). The reaction mixture was heated at 45° C. for 18 h, then allowed to cool to room temperature, and concentrated in vacuo. The residue was absorbed on silica gel, the free running powder was placed on a 10 g isolute silica column which was eluted with ethyl acetate/dichloromethane (v/v; 1:1). The title compound was obtained as an orange solid (0.054 g, 60%); 1H-NMR (500 MHz, DMSO-d6) 0.87 (d, J=6.57 Hz, 6H, CH(CH3)2), 1.77 (m, 1H, CH(CH3)2), 2.08 (d, J=7.39 Hz, 2H, N—CH2), 2.45 (br s, 4H, piperazine N(CH2)2), 3.05 (br s, 4H, piperazine N(CH2)2), 6.94 (s, 2H, NH2), 8.06 (s, 1H, 6-H);

Aufarbeitung

temperatureto cool to room temperature
concentrationconcentrated in vacuo
customThe residue was absorbed on silica gel
washwas eluted with ethyl acetate/dichloromethane (v/v; 1:1)

Quellen und Nachweise

ORD-Eintrag: ord-6972cfd36dad47a0965f7abe9915649f
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08088761B2

Verknüpfte Notizen

Wird geladen…