Piperidine → HCID 178496943, Verbindung

HRID 577801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577801
C([N:4]1[C:12]2[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[N:9]=[CH:8][C:7]=2/[C:6](=[C:17](\OCC)/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)/[C:5]1=[O:27])(=O)C.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]([CH3:46])[C:36](=[O:45])[CH2:37][N:38]2[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]2)=[CH:31][CH:30]=1.N1CCCCC1>CN(C=O)C>[CH3:46][N:35]([C:32]1[CH:31]=[CH:30][C:29]([NH:28]/[C:17](/[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:6]2\[C:5](=[O:27])[NH:4][C:12]3[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[N:9]=[CH:8][C:7]\2=3)=[CH:34][CH:33]=1)[C:36](=[O:45])[CH2:37][N:38]1[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]1

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 21927707N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamideHCID 89719567(E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate

Produkt 1

HCID 178496943HCID 178496943, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Step-2: To a solution of (E)-methyl 1-acetyl-3-(ethoxy(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (40 mg, 0.109 mmol) in DMF (0.2 mL) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (28 mg, 0.109 mmol) at room temperature, and the reaction mixture was stirred at 110° C. for 2 h. The reaction mixture was cooled to RT, piperidine (0.2 mL) was added and stirred for 10 minutes at room temperature. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography using 5% CH3OH in dichloromethane as eluent to afford (Z)-methyl 3-(((4-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)phenyl)amino)(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-6-carboxylate as yellow solid. MS (ES+): m/z 541.3 (MH+).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. stirringstirred for 10 minutes at room temperature
  3. customThe solvent was evaporated
  4. customthe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b057825dfa5c42cba85dad529fad6974
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040555B2

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