N-[3-(4-(2-chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanoyl]-2-(dimethylamino)ethanesulfonamide → N-[3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanoyl]-2-(dimethylamino)ethanesulfonamide

HRID 11108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11108
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26]C)[CH:14]=[CH:13][C:12]=3[N:11]([CH2:28][CH2:29][C:30]([NH:32][S:33]([CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])(=[O:35])=[O:34])=[O:31])[C:10]=2[CH:9]=1>C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:28][CH2:29][C:30]([NH:32][S:33]([CH2:36][CH2:37][N:38]([CH3:39])[CH3:40])(=[O:35])=[O:34])=[O:31])[C:10]=2[CH:9]=1

Komponenten

3

Edukt 1

HCID 86760206N-[3-(4-(2-chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanoyl]-2-(dimethylamino)ethanesulfonamide

Produkt 1

HCID 10415573N-[3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)propanoyl]-2-(dimethylamino)ethanesulfonamideAusbeute 23,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Reaction of methyl ether (267) (35 mg, 0.06 mmol) prepared as described in example 224 according to the proceedure described in example 81, except that the reaction mixture was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with methanol/dichloromethane (1:9 to 1:3), gave acylsulfonamide (271) (8 mg, 23%) as an orange powder, mp 229–233° C. 1H NMR δ [(CD3)2SO] 11.05 (br s, 1H), 9.37 (br s, 1H), 8.37 (d, J=2.5 Hz, 1H), 7.74 (s, 1H), 7.61–7.52 (m, 3H), 7.50–7.43 (m, 2H), 7.14 (dd, J=8.7, 2.5 Hz, 1H), 4.63 (m, 2H), 3.21 (partially obscured m, 2H), 2.81 (m, 2H), 2.59 (t, J=6.8 Hz, 2H), 2.38 (s, 6H). FABMS found [M+H]+: 569.1255, 571.1204. C27H25ClN4O6S requires 569.1262, 571.1232.

Aufarbeitung

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. customthe drying agent was removed
  5. concentrationthe solution was concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-786dafbcfc7b4dec85251560283dc0a9
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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