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
Reaction equation
[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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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).
Workup
- custombefore quenching with aqueous ammonium chloride and extraction into dichloromethane
- dry with materialThe organic phase was dried (MgSO4)
- filtrationfiltered
- customevaporated
- customto give the crude product as a colourless oil
Sources & evidence
- ORD record
- ord-78a5f356e2054172b77586bf558d71f1
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662825B2
Reaction notes
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