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 → n-[2-(Dimethylamino)ethyl]-3-(9-hydroxy-4-(2-methoxyphenyl)-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)propanamide

HRID 11107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11107
Cl[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]([CH2:29][CH2:30][C:31]([NH:33][CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])=[O:32])[C:12]=2[CH:11]=1>C(OCC)(=O)C.CO.[Pd]>[CH3:38][N:36]([CH3:37])[CH2:35][CH2:34][NH:33][C:31](=[O:32])[CH2:30][CH2:29][N:13]1[C:12]2[CH:11]=[C:10]([C:3]3[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=3[O:8][CH3:9])[C:22]3[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=3[C:20]=2[C:19]2[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]1=2

Komponenten

4

Edukt 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]propanamide

Produkt 1

HCID 69583799n-[2-(Dimethylamino)ethyl]-3-(9-hydroxy-4-(2-methoxyphenyl)-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1h)-yl)propanamideAusbeute 17,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

To a solution of amide (260) (40 mg, 0.07 mmol)) prepared as described in example 219 in ethyl acetate/methanol (1:1, 80 mL) was added 5% Pd-C (catalytic). The resulting suspension was hydrogenated at 60 psi with stirring for 4 days, with additional portions of Pd-C being added every 24 hours. The reaction mixture was then filtered through celite and concentrated under reduced pressure before being chromatographed on silica eluting with methanol/ethyl acetate/triethylamine (1:4:trace), to give amide (330) (6 mg, 16%) as a yellow powder, mp 232–238° C. 1H NMR δ [(CD3)2SO] 10.95 (br s, 1H), 9.33 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 8.01 (br s, 1H), 7.69 (s, 1H), 7.54 (d, J=8.9 Hz, 1H), 7.43 (m, 1H), 7.34 (dd, J=7.5, 1.8 Hz, 1H), 7.13–7.05 (m, 3H), 4.67 (t, J=6.2 Hz, 2H), 3.69 (s, 3H), −3.2 (obscured m, 2H), 2.60 (t, J=6.2 Hz, 2H), 2.54–2.49 (obscured m, 8H). FABMS found [M+H]+: 501.2142. C28H28N4O5 requires 501.2138.

Aufarbeitung

  1. additionadded every 24 hours
  2. filtrationThe reaction mixture was then filtered through celite and
  3. concentrationconcentrated under reduced pressure
  4. custombefore being chromatographed on silica eluting with methanol/ethyl acetate/triethylamine (1:4:trace)

Quellen und Nachweise

ORD-Eintrag
ord-2d72889ef0374e16a7cf146871cfef15
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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