Methanesulfonyl chloride → (+/-)-6-Methoxy-2-methyl-3-[1-(methylsulfonyl)piperidin-3-yl]-4-phenylisoquinolin-1(2H)-one

HRID 17869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 17869
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH3:14])[C:7]([CH:15]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]1)=[C:6]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH3:14])[C:7]([CH:15]1[CH2:20][CH2:19][CH2:18][N:17]([S:37]([CH3:36])(=[O:39])=[O:38])[CH2:16]1)=[C:6]2[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

6

Edukt 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 11279492(+/-)-6-Methoxy-2-methyl-4-phenyl-3-piperidin-3-ylisoquinolin-1(2H)-one

Produkt 1

HCID 11327779(+/-)-6-Methoxy-2-methyl-3-[1-(methylsulfonyl)piperidin-3-yl]-4-phenylisoquinolin-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a methylene chloride (0.100 mL) solution of (±)-6-methoxy-2-methyl-4-phenyl-3-piperidin-3-ylisoquinolin-1(2H)-one (30 mg, 0.086 mmol) and N,N-diisopropylethylamine (0.017 mL, 0.095 mmol) was added methanesulfonyl chloride (0.007 mL, 0.095 mmol). After 24 hours saturated sodium bicarbonate and additional methylene chloride were added. The layers were separated and the organic phase dried with anhydrous magnesium sulfate. Evaporation of the solvent in vacuo followed by trituration with ether-EtOAc gave a white solid which was isolated by vacuum filtration to give the titled product. ESI+MS: 427.1 [M+H]+.

Aufarbeitung

  1. customThe layers were separated
  2. dry with materialthe organic phase dried with anhydrous magnesium sulfate
  3. customEvaporation of the solvent in vacuo
  4. customgave a white solid which
  5. customwas isolated by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-6c3f74d63301475dbdfd131f9419fa5c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741322B2

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