5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-3-methylpyrazine-2-carboxylic acid, methyl ester → 2,3-Dichloro-N-[5-(hydroxymethyl)-3-methoxy-6-methyl-2-pyrazinyl)benzenesulphonamide

HRID 1444023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1444023
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[N:14]=[C:15]([CH3:25])[C:16]([C:21](OC)=[O:22])=[N:17][C:18]=1[O:19][CH3:20])(=[O:11])=[O:10].C([BH-](CC)CC)C.[Li+].ClCCl.C(OCC)(=O)C.C(O)(=O)C>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18]([O:19][CH3:20])=[N:17][C:16]([CH2:21][OH:22])=[C:15]([CH3:25])[N:14]=1)(=[O:10])=[O:11]

Komponenten

5

Edukt 3

HCID 101730625-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-3-methylpyrazine-2-carboxylic acid, methyl esterHCID 21963926CH2Cl2 EtOAc AcOHHCID 23664628Lithiumtriethylborohydride

Produkt 1

HCID 102871922,3-Dichloro-N-[5-(hydroxymethyl)-3-methoxy-6-methyl-2-pyrazinyl)benzenesulphonamideAusbeute 214,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 5-(2,3-dichlorobenzenesulphonylamino)-6-methoxy-3-methylpyrazine-2-carboxylic aicd, methyl ester (Example 119) (0.19 g) in tetrahydrofuran (10 mL) under an atmosphere of nitrogen was added a solution of lithium triethylborohydride (1.7 mL of a 1M solution in tetrahydrofuran). The reaction mixture was stirred at room temperature for 1 h, before quenching with aqueous ammonium chloride and extraction into dichloromethane. The organic phase was dried (MgSO4), filtered and evaporated to give the crude product as a colourless oil. Chromatography on silica gel eluting with dichloromethane/ethyl acetate/acetic acid (150:50: 1) gave the title compound as a white solid (0.38 g).

Aufarbeitung

  1. custombefore quenching with aqueous ammonium chloride and extraction into dichloromethane
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give the crude product as a colourless oil

Quellen und Nachweise

ORD-Eintrag
ord-78a5f356e2054172b77586bf558d71f1
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662825B2

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