Piperazine → 9-Hydroxy-4-phenyl-6-[3-(1-piperazinyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11095
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]3[C:24](=[O:28])[NH:25][C:26](=[O:27])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:29])[CH:8]=[CH:7][C:6]1=2.[NH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[OH:29][C:9]1[CH:8]=[CH:7][C:6]2[N:5]([CH2:4][CH2:3][CH2:2][N:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:17]3[CH:16]=[C:15]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:14]4[C:24](=[O:28])[NH:25][C:26](=[O:27])[C:13]=4[C:12]=3[C:11]=2[CH:10]=1

Komponenten

3

Edukt 2

HCID 4837PiperazineHCID 867602016-(3-Bromopropyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Produkt 1

HCID 219804049-Hydroxy-4-phenyl-6-[3-(1-piperazinyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneAusbeute 55 %

Versuchsvorschrift

Bromide (204) (70 mg, 0.16 mmol) prepared as described in example 173 was reacted with piperazine according to The procedure described in example 179 except that the reaction was performed at room temperature for 20 h, to give amine (215) (40 mg, 55%) as a yellow powder, mp 178–183° C. 1H NMR δ [(CD3)2SO] 11.0 (br s, 1H), 9.35 (br s, 1H), 8.40 (d, J=2.4 Hz, 1H), 7.78 (s, 1H), 7.62 (m, 2H), 7.56 (d, J=8.8 Hz, 1H), 7.45 (m, 3H), 7.14 (dd, J=8.8, 2.4 Hz, 1H), 4.49 (t, J=6.3 Hz, 2H), 2.52 (m, 4H), 2.12 (m, 6H), 1.91 (m, 2H). Found: C, 69.31; H, 5.97; N, 11.49. C27H26N4O3.4/5H2O requires: C, 69.16; H, 5.93; N, 11.94.

Quellen und Nachweise

ORD-Eintrag
ord-2a3230ac66084754a1ba89fe21f7b805
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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