Potassium Carbonate → 4-{[(4-Chloro-benzenesulfonyl)-(5-isopropyl-2-oxo-azepan-3-yl)-amino]-methyl}-benzamide

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Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:18][CH:17]([CH:19]([CH3:21])[CH3:20])[CH2:16][CH2:15][NH:14][C:13]2=[O:22])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH2:30])=[O:29])=[C:26](C)[CH:25]=1.[C:34]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:34][C:24]2[CH:25]=[CH:26][C:27]([C:28]([NH2:30])=[O:29])=[CH:31][CH:32]=2)[CH:12]2[CH2:18][CH:17]([CH:19]([CH3:20])[CH3:21])[CH2:16][CH2:15][NH:14][C:13]2=[O:22])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

4-Chloro-N-(5-isopropyl-2-oxo-azepan-3-yl)-benzenesulfonamide (0.06 g, 0.17 mmol), 4-bromo-methyl-benzamide (0.06 g, 0.25 mmol), K2CO3 (0.24 g, 1.7 mmol), KI (0.01 g, 0.06 mmol) were added to dry DMF (5 ml) and the resultant reaction mixture was shaken overnight at 65° C. under an argon atmosphere. The solvent was removed under reduced pressure and the residue taken up in ethyl acetate and washed with 5% KHSO4/10% K2SO4 (2×), water, brine, dried (MgSO4), filtered, concentrated under reduced pressure and purified using preparative RP(C18) chromatography: lyophilisate 23 mg; MS: m/e=478.3 (MH+), 495.4 (MNH4+)

Aufarbeitung

customthe resultant reaction mixture
customThe solvent was removed under reduced pressure
washwashed with 5% KHSO4/10% K2SO4 (2×), water, brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified

Quellen und Nachweise

ORD-Eintrag: ord-7b475eeaec1b4a0cbd8a0514248b3189
Quelldatensatz: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07253158B2

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