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

HRID 851981Notes

Reaction equation

[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

Participants

Conditions

Temperature: 65 °C

Procedure

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+)

Workup

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

Sources & evidence

ORD record: ord-7b475eeaec1b4a0cbd8a0514248b3189
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253158B2

Reaction notes

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