1,1'-Carbonyldiimidazole → 2-(4-(4,9-diethoxy-1-oxo-1H-benzo[f]isoindol-2(3H)-yl)phenyl)-N-((4-fluorophenyl)sulfonyl)acetamide

HRID 346711

Reaktionsgleichung

Reaktionsgleichung von HRID 346711
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:15][C:16]1[C:24]2[CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=3)[C:21](=[O:35])[C:20]=2[C:19]([O:36][CH2:37][CH3:38])=[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=12)[CH3:14].[F:43][C:44]1[CH:49]=[CH:48][C:47]([S:50]([NH2:53])(=[O:52])=[O:51])=[CH:46][CH:45]=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH2:13]([O:15][C:16]1[C:24]2[CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH:53][S:50]([C:47]4[CH:46]=[CH:45][C:44]([F:43])=[CH:49][CH:48]=4)(=[O:52])=[O:51])=[O:33])=[CH:27][CH:26]=3)[C:21](=[O:35])[C:20]=2[C:19]([O:36][CH2:37][CH3:38])=[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=12)[CH3:14]

Komponenten

6

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 1202314-FluorobenzenesulfonamideHCID 9931112[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid

Produkt 1

HCID 98940822-(4-(4,9-diethoxy-1-oxo-1H-benzo[f]isoindol-2(3H)-yl)phenyl)-N-((4-fluorophenyl)sulfonyl)acetamideAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of carbonyldiimidazole (13.2 mg, 0.081 mmol) and [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid (30 mg, 0.074 mmol) in dichloromethane (2 ml) was added 4-fluorobenzenesulphonamide (14.3 mg, 0.081 mmol) and N,N-diisopropylethylamine (10.5 mg, 0.81 mmol). The mixture was stirred at ambient temperature under an atmosphere of nitrogen overnight. The reaction mixture was diluted with dichloromethane (3 ml) and then washed with 2N hydrochloric acid (5 ml). The organic phase was dried (MgSO4) and then concentrated in vacuo to give a brown gum. The residue was purified using mass directed autopurification to give the title compound as a white solid (14.7 mg, 35.3%). MH+563.

Aufarbeitung

  1. washwashed with 2N hydrochloric acid (5 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give a brown gum
  5. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-74fcd33b573a41169ca8bf9fead8c9a7
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173047B2

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