Morpholine → 9-hydroxy-6-(3-morpholinopropyl)-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11090
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][O: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][O:33][CH2:32][CH2:31]3)[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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 8083MorpholineHCID 867602016-(3-Bromopropyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Produkt 1

HCID 219803779-hydroxy-6-(3-morpholinopropyl)-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneAusbeute 72 %

Versuchsvorschrift

Bromide (204) (0.01 g, 0.22 mmol) prepared as described in example 173 was reacted with morpholine according to the procedure described in example 179 to give amine (210) (73 mg, 72%) as a yellow powder, mp 252–255° C. 1H NMR δ [(CD3)2SO] 11.04 (br s, 1H), 9.33 (s, 1H), 8.41 (d, J=2.5 Hz, 1H), 7.81 (s, 1H), 7.62 (m, 2H), 7.57 (d, J=8.9 Hz, 1H), 7.47 (m, 3H), 7.12 (dd, J=8.9, 2.5 Hz, 1H), 4.51 (t, J=6.3 Hz, 2H), 3.38 (t, J=4.0 Hz, 4H), 2.18 (br s, 4H), 2.14 (t, J=6.3 Hz, 2H), 1.93 (m, 2H). Found: C, 71.11; H, 5.46; N, 9.29. C27H25N3O4 requires: C, 71.19; H, 5.53; N, 9.22.

Quellen und Nachweise

ORD-Eintrag
ord-d4de17759f9b43b7a5dcf2c935b7db3d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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