6-(3-(1H-imidazol-1-yl)propyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione → 3-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)-n-[2-(dimethylamino)ethyl]propanamide

HRID 11106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11106
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([O:28]C)[CH:16]=[CH:15][C:14]=3[N:13]([CH2:30][CH2:31][C:32]([NH:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[O:33])[C:12]=2[CH:11]=1.OC1C=CC2N(CCCN3C=CN=C3)C3C=C(C4C=CC=CC=4)C4C(=O)NC(=O)C=4C=3C=2C=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]=3[N:13]([CH2:30][CH2:31][C:32]([NH:34][CH2:35][CH2:36][N:37]([CH3:39])[CH3:38])=[O:33])[C:12]=2[CH:11]=1

Komponenten

3

Edukt 2

HCID 219806586-(3-(1H-imidazol-1-yl)propyl)-9-hydroxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 91312222HCID 91312222, Verbindung

Produkt 1

HCID 117569303-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)-n-[2-(dimethylamino)ethyl]propanamideAusbeute 83 %

Versuchsvorschrift

Reaction of methyl ether (252) prepared as described in example 212 (80 mg, 0.15 mmol) according to The procedure described in example 80, except that the reaction was performed at 0° C. for 2 hours and chromatography was performed eluting with ethyl acetate/methanol/triethylamine (1:0:0 to 3:1:trace), gave amide (260) (65 mg, 83%) as a yellow/orange powder, mp 200–205° C. 1H NMR δ [(CD3)2SO] 11.00 (br s, 1H), 9.34 (s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.87 (br s, 1H), 7.66 (s, 1H), 7.54 (d, J=8.9 Hz, 1H), 7.44 (t, J=8.2 Hz, 1H), 7.18 (dd, J=8.2, 0.7 Hz, 1H), 7.12 (m, 2H), 4.64 (t, J=6.6 Hz, 2H), 3.68 (s, 3H), 3.05 (m, 2H), 2.56 (t, J=6.6 Hz, 2H), 2.23 (v br s, 2H), 2.15 (br s, 6H). Found: C, 58.98; H, 5.12; N, 9.59. C28H27ClN4O5.2H2O requires: C, 58.90; H, 5.47; N, 9.81.

Aufarbeitung

  1. customprepared
  2. washchromatography was performed eluting with ethyl acetate/methanol/triethylamine (1:0:0 to 3:1:trace)

Quellen und Nachweise

ORD-Eintrag
ord-66d5617ee3174b04900152f40608af0f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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