Piretanide → HCID 11575958, compound

HRID 1676920Notes

Reaction equation

HRID 1676920 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([O:7][C:8]2[C:9]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:10][C:11]([C:18]([OH:20])=[O:19])=[CH:12][C:13]=2[S:14]([NH2:17])(=[O:16])=[O:15])=[CH:5][CH:6]=1.Cl.[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31]Cl.C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O>[NH2:17][S:14]([C:13]1[CH:12]=[C:11]([CH:10]=[C:9]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[C:8]=1[O:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:18]([O:20][CH2:31][CH2:30][CH2:29][N:28]([CH3:33])[CH3:27])=[O:19])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 4849PiretanideHCID 5238Sodium IodideHCID 8471TriethylamineHCID 943083-(Dimethylamino)propyl chloride hydrochloride

Product 1

HCID 11575958HCID 11575958, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 31, piretanide can be reacted with 3-(dimethylamino)propyl chloride hydrochloride, triethylamine and sodium iodide in dimethylformamide (DMF) to yield 3-(N,N-dimethylaminopropyl 3-aminosulfonyl-4-phenoxy-5-(1-pyrrolidinyl)benzoate.

Sources & evidence

ORD record
ord-24ff1b0503714307a7845621ef601430
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Reaction notes

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