Methyl 2-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonylamino)sulfonyl]-6-nitrobenzoate → Methyl 2-amino-6-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonylamino)-sulfonyl]benzoate
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]([NH:14][S:15]([C:18]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[C:19]=2[C:20]([O:22][CH3:23])=[O:21])(=[O:17])=[O:16])=[O:13])[N:4]=1>CO.CN(C)C=O.[Pd].[O-][V](=O)=O.[Na+]>[NH2:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:18]([S:15]([NH:14][C:12]([NH:11][C:5]2[N:6]=[C:7]([O:9][CH3:10])[N:8]=[C:3]([O:2][CH3:1])[N:4]=2)=[O:13])(=[O:16])=[O:17])[C:19]=1[C:20]([O:22][CH3:23])=[O:21]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
50 mg (113 μmol) of methyl 2-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]-carbonylamino)sulfonyl]-6-nitrobenzoate are suspended in a mixture of 3 ml of methanol/dimethylformamide (5:1), admixed with 10 mg. of palladium on activated carbon (5%) and 1 mg (8.20 μmol) of sodium (meta)vanadate and, hydrogenated under atmospheric pressure and at room temperature for 3 h. The mixture is then filtered off, the filtrate is concentrated and the residue is taken up in water and adjusted to pH 1.5 using 3 N aqueous hydrochloric acid solution. The precipitate is stirred in an ice-bath for 10 min and then filtered off with suction and dried under reduced pressure. This gives 41 mg (87% of theory) of methyl 2-amino-6-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonylamino)sulfonyl]benzoate of m.p. 129-134° C. (decomp.).
Workup
- filtrationThe mixture is then filtered off
- concentrationthe filtrate is concentrated
- filtrationfiltered off with suction
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-de89b241022b4f808fbde7150608d32c
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414011B2
Reaction notes
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