Methyl iodide → 7-Methoxynaphthalene-2-sulfonic acid [1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-methylamide

HRID 651600

Reaktionsgleichung

Reaktionsgleichung von HRID 651600
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:17][CH2:16][C@H:15]([NH:18][S:19]([C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([O:32][CH3:33])=[CH:27][CH:28]=5)[CH:23]=4)(=[O:21])=[O:20])[C:14]3=[O:34])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:35](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:17][CH2:16][C@H:15]([N:18]([CH3:35])[S:19]([C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([O:32][CH3:33])=[CH:27][CH:28]=5)[CH:23]=4)(=[O:20])=[O:21])[C:14]3=[O:34])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 155458317-Methoxy-naphthalene-2-sulfonic acid[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(s)-yl]-amide

Produkt 1

HCID 571517637-Methoxynaphthalene-2-sulfonic acid [1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-methylamideAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-methoxynaphthalene-2-sulfonic acid [1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide (0.151 g, 0.304 mmol) in acetone (20 mL) is added potassium carbonate (0.084 g, 0.608 mmol) followed by methyl iodide (0.12 mL, 1.93 mmol). The resulting mixture is heated to reflux overnight, then cooled to room temperature and diluted with methylene chloride. The solution is washed with saturated NaHCO3 solution, water and brine. The organic layer is dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography eluting with 5% MeOH/CH2Cl2 to give the product (0.093 mg, 0.18 mmol) as an oil.

Aufarbeitung

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux overnight
  3. washThe solution is washed with saturated NaHCO3 solution, water and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by column chromatography
  8. washeluting with 5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-f82e18e090d44227aee6525dd6c6293f
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281227B1

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