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 11108ノート

反応式

HRID 11108 の反応式
[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

参加物

3

反応物 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

生成物 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)ethanesulfonamide収率 23.4%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-786dafbcfc7b4dec85251560283dc0a9
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

反応ノート

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