Potassium Iodide → 8-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-5,6-dihydro-3H-benzo[f]cinnolin-2-one

HRID 2042644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042644
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:20]=[CH:19][C:9]2[C:10]3[C:15]([CH2:16][CH2:17][C:8]=2[CH:7]=1)=[N:14][NH:13][C:12](=[O:18])[CH:11]=3.[CH3:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][NH2+:23]1.C1(S([O-])(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:20]=[CH:19][C:9]2[C:10]3[C:15]([CH2:16][CH2:17][C:8]=2[CH:7]=1)=[N:14][NH:13][C:12](=[O:18])[CH:11]=3

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 596519478-(3-Chloro-propoxy)-5,6-dihydro-3H-benzo[f]cinnolin-2-oneHCID 86646919(R)-2-methylpyrrolidine benzene sulfonate

Produkt 1

HCID 249947458-[3-((R)-2-Methyl-pyrrolidin-1-yl)-propoxy]-5,6-dihydro-3H-benzo[f]cinnolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a 25 mL round bottom flask, 8-(3-chloro-propoxy)-5,6-dihydro-3H-benzo[f]cinnolin-2-one (100 mg, 0.34 mmol), benzenesulfonate (R)-2-methyl-pyrrolidinium (168 mg, 0.68 mmol), potassium carbonate (190 mg, 1.36 mmol), and potassium iodide (1 mg, 0.006 mmol) in acetonitrile (10 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, and then washed with water 3 times. The organics were chromatographed through silica gel with methylene chloride/methanol (95:5) eluent to produce 10 mg (9%). Mp 225° C. (dec.). MS m/z 340 (M+H).

Aufarbeitung

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customThe slurry was partitioned between methylene chloride and water
  5. washwashed with water 3 times
  6. customThe organics were chromatographed through silica gel with methylene chloride/methanol (95:5) eluent
  7. customto produce 10 mg (9%)

Quellen und Nachweise

ORD-Eintrag
ord-a95066b91c994445a6cc48dcf3d29c7b
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586588B2

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