Potassium Iodide → 4-chloro-N-(2-oxo-azepan-3-yl)-N-(4-pyrazol-1-yl-benzyl)-benzenesulfonamide

HRID 851991Notes

Reaction equation

HRID 851991 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[CH:31][CH:30]=[N:29]2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([N:28]3[CH:32]=[CH:31][CH:30]=[N:29]3)=[CH:26][CH:27]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27386834-Chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamideHCID 27764791-[4-(Bromomethyl)Phenyl]-1H-Pyrazole

Product 1

HCID 694892494-chloro-N-(2-oxo-azepan-3-yl)-N-(4-pyrazol-1-yl-benzyl)-benzenesulfonamideYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-N-(2-oxo-azepan-3-yl)-benzenesulfonamide (0.16 g, 0.52 mmol), 1-[4-(bromomethyl)phenyl]-1H-pyrazole (0.26 g, 1.03 mmol), potassium carbonate (0.72 g, 5.17 mmol) and potassium iodide (0.02 g, 0.10 mmol) in 5 ml dimethylformamide were stirred at 65° C. for 5 hours. Extraction with water/ethylacetate and chromatography on silicagel with ethylacetate/heptane (90/10 to 1/0) yielded 0.20 g (87%) 4-chloro-N-(2-oxo-azepan-3-yl)-N-(4-pyrazol-1-yl-benzyl)-benzenesulfonamide as light yellow solid, MS: m/e (%)=459.1 (MH+, 100).

Workup

  1. extractionExtraction with water/ethylacetate and chromatography on silicagel with ethylacetate/heptane (90/10 to 1/0)

Sources & evidence

ORD record
ord-d9fd94ff77b3455fbd035414419c0093
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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