Azosemide → 5-[1-(t-Butylcarbonyloxymethyl)-1H-tetrazol-5-yl]-2-chloro-4-[(2-thienylmethyl)amino]benzenesulfonamide

HRID 1676935

Reaction equation

HRID 1676935 reaction equation
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[C:13]([C:14]3[N:18]=[N:17][NH:16][N:15]=3)=[CH:12][C:11]([S:19]([NH2:22])(=[O:21])=[O:20])=[C:10]([Cl:23])[CH:9]=2)[S:4][CH:5]=1.[C:24]([O:30][CH2:31]Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C.[I-].[Na+]>CN(C=O)C>[C:25]([C:24]([O:30][CH2:31][N:15]1[C:14]([C:13]2[C:8]([NH:7][CH2:6][C:3]3[S:4][CH:5]=[CH:1][CH:2]=3)=[CH:9][C:10]([Cl:23])=[C:11]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:12]=2)=[N:18][N:17]=[N:16]1)=[O:29])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 2273AzosemideHCID 5238Sodium IodideHCID 8471TriethylamineHCID 87885Chloromethyl pivalate

Product 1

HCID 602084215-[1-(t-Butylcarbonyloxymethyl)-1H-tetrazol-5-yl]-2-chloro-4-[(2-thienylmethyl)amino]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 12, azosemide can be reacted with chloromethyl pivalate, triethylamine and sodium iodide in DMF to yield 5-[1-(t-Butylcarbonyloxymethyl)-1H-tetrazol-5-yl]-2-chloro-4-[(2-thienylmethyl)amino]benzenesulfonamide.

Sources & evidence

ORD record
ord-0c1dfbcca0684062a244ca47d8938754
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Linked notes

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