Bumetanide → HCID 16657633, compound

HRID 1676916Notes

Reaction equation

HRID 1676916 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:23]([OH:25])=[O:24])[CH:9]=[C:10]([S:19]([NH2:22])(=[O:21])=[O:20])[C:11]=1[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.[C:26]([O:30][CH2:31]Cl)(=[O:29])[CH2:27][CH3:28].C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O>[NH2:22][S:19]([C:10]1[CH:9]=[C:8]([CH:7]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:23]([O:25][CH2:31][O:30][C:26]([CH2:27][CH3:28])=[O:29])=[O:24])(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 2471BumetanideHCID 5238Sodium IodideHCID 8471TriethylamineHCID 221144Chloromethyl propionate

Product 1

HCID 16657633HCID 16657633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 12, bumetanide can be reacted with chloromethyl propionate, triethylamine and sodium iodide in dimethylformamide (DMF) to yield ethylcarbonyloxymethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate.

Sources & evidence

ORD record
ord-c42c640127834aaab489b5e7114cb52f
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Reaction notes

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