Potassium Carbonate → 4-{[(4-Chloro-benzenesulfonyl)-((R)-2-oxo-azepan-3-yl)-amino]-methyl}-benzamide

HRID 851974Notes

Reaction equation

HRID 851974 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H: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[C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[C:23](C)[CH:22]=1.[C:31]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:31][C:21]2[CH:22]=[CH:23][C:24]([C:25]([NH2:27])=[O:26])=[CH:28][CH:29]=2)[C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69279554-Chloro-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamideHCID 206167664-Bromo-2-methylbenzamide

Product 1

HCID 115972674-{[(4-Chloro-benzenesulfonyl)-((R)-2-oxo-azepan-3-yl)-amino]-methyl}-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloro-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamide (0.18 g, 0.60 mmol), 4-bromo-methyl-benzamide (0.19 g, 0.90 mmol), K2CO3 (0.83 g, 6 mmol), KI (0.02 g, 0,12 mmol) were added to dry DMF (15 ml) and the resultant reaction mixture was shaken overnight at 60° C. under an argon atmosphere. The solvent was removed under reduced pressure and the residue dissolved in acetonitrile and purified using preparative RP(C18) chromatography: lyophilisate 52 mg; MS: m/e=436.4 (MH+)

Workup

  1. customthe resultant reaction mixture
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue dissolved in acetonitrile
  4. custompurified

Sources & evidence

ORD record
ord-d1c7fc492f514d59b9f91982c0fe62a8
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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