Reaktion #11204

Reaktionsgleichung

methyl ether

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

→

acylsulfonamide

Ausbeute 23.4%

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

Ausbeute 23.4%

Lösungsmittel

sodium bicarbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   SonstigeThe organic phase was dried
4. 4
   Sonstigethe drying agent was removed
5. 5
   Einengenthe solution was concentrated to dryness

Vorschrift

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.

Quelle