Mafenide → HCID 69586563, compound

HRID 723118Notes

Reaction equation

HRID 723118 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:21][CH3:22])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16](Cl)=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[NH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C.C1COCC1>CO.C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:21][CH3:22])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][C:16]([NH:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([S:31](=[O:33])(=[O:32])[NH2:34])=[CH:29][CH:30]=3)=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 3998MafenideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 210571794-(5-Bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 69586563HCID 69586563, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

The reaction was conducted following the procedure for Example 156: step a, using. 4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (0.050 g, 0.113 mmol), (Example 2: step c), 4-aminomethyl-benzenesulfonamide (0.033 g, 0.146 mmol), diisopropylethylamine (0.073 g, 0.565 mmol), THF [0.5 mL], DMF [0.5 mL]. Chromatography of the residue (0%–5% MeOH/DCM) yielded the title compound. ESI-MS (m/z): Calcd. for C19H18BrN3O6S4: 592.53 (M+H); found 592.0, 593.9.

Sources & evidence

ORD record
ord-d2db53a5859a4ae5a1ca377f9aa79a38
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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