Piretanide → HCID 11619255, compound

HRID 1676926Notes

Reaction equation

HRID 1676926 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[CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29].C(N(CC)CC)C.[I-].[Na+]>CN(C=O)C>[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][CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29])=[O:19])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 4849PiretanideHCID 5238Sodium IodideHCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 11619255HCID 11619255, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 11, piretanide can be reacted with 2-chloro-N,N dimethylacetamide, triethylamine and sodium iodide in DMF to yield N,N-dimethylaminocarbonylmethyl 3-aminosulfonyl-4-phenoxy-5-(1-pyrrolidinyl)benzoate.

Sources & evidence

ORD record
ord-9284a6d0963b4966acd4e2aa6f8d216d
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Reaction notes

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