Acetic Acid → 2,3-Dichloro-N-[5-(hydroxymethyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

HRID 1444042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1444042
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[N:20]=[CH:21][C:22]([C:33](OC)=[O:34])=[N:23][C:24]=1[O:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)(=[O:17])=[O:16].C(O)(=O)C>O1CCCC1>[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[S:15]([NH:18][C:19]1[C:24]([O:25][CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[N:23][C:22]([CH2:33][OH:34])=[CH:21][N:20]=1)(=[O:17])=[O:16]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 21226445Aluminium lithium hydrideHCID 59168105HCID 59168105, Verbindung

Produkt 1

HCID 591682022,3-Dichloro-N-[5-(hydroxymethyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamideAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-65 °C

Versuchsvorschrift

Lithium aluminium hydride (0.85 mL of a 1M solution in tetrahydrofuran) was added dropwise to 5-(2,3-dichlorobenzenesulphonylamino)-6-(3-pyridinylmethoxy)pyrazine-2-carboxylic acid, methyl ester (Example 134) (0.2 g) in tetrahydrofuran (10 mL) cooled to −65° C. The reaction mixture was allowed to warm to room temperature and stirred for 1h. Aqueous acetic acid was added and the mixture extracted with ethyl acetate. The organic solution was dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/methanol mixtures gave the title compound (0.08 g).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-34fa62a8e8954656841e510c9930ab45
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662825B2

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