Dimethylformamide → n-(4-Methanesulfonylamino-2-sulfamoylphenyl)malonamic acid methyl ester

HRID 2410633Notes

Reaction equation

HRID 2410633 reaction equation
CN(C=O)C.CC(N(C)C)=O.[CH3:12][O:13][C:14](=[O:30])[CH2:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=1[S:26](=[O:29])(=[O:28])[NH2:27])=[O:17].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1.CN1C(=O)CCC1.C1COCC1>[CH3:12][O:13][C:14](=[O:30])[CH2:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:21][C:20]=1[S:26](=[O:29])(=[O:28])[NH2:27])=[O:17]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 31297Methanesulfonyl chlorideHCID 31374DimethylacetamideHCID 86762633HCID 86762633, compound2×

Product 1

HCID 24858399n-(4-Methanesulfonylamino-2-sulfamoylphenyl)malonamic acid methyl ester

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

reducing the N-(4-nitro-2-sulfamoyl-phenyl)-malonamic acid methyl ester (III), via a catalyst in the presence of an polar aprotic solvent or polar aprotic solvent mixture, to form N-(4-amino-2-sulfamoyl-phenyl)-malonamic acid methyl ester (IV), wherein the aprotic solvent is selected from the group consisting of DMF, DMA, THF, NMP or solvent mixtures thereof, and is more preferably a solvent mixture, and d. mesylating the N-(4-amino-2-sulfamoyl-phenyl)-malonamic acid methyl ester (IV), via addition of methanesulfonyl chloride to a suspension of N-(4-amino-2-sulfamoyl-phenyl)-malonamic acid methyl ester (IV) and pyridine to form the intermediate compound N-(4-methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid methyl ester (V).

Sources & evidence

ORD record
ord-09ba454c694849e1bc66f11c966d2c4e
Source dataset
uspto-grants-2014_08
Patent number
US08816120B2

Reaction notes

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