Benzenesulfonyl chloride, 3,4-dichloro- → 3,4-dichloro-N-[5-chloro-2-(2-chloro-benzoyl)-pyridin-3-yl]-benzenesulfonamide

HRID 1438491Notizen

Reaktionsgleichung

[NH2:1][C:2]1[C:3]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[O:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:18][C:19]1[CH:20]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[Cl:25]>N1C=CC=CC=1>[Cl:18][C:19]1[CH:20]=[C:21]([S:26]([NH:1][C:2]2[C:3]([C:9](=[O:10])[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=2)(=[O:27])=[O:28])[CH:22]=[CH:23][C:24]=1[Cl:25]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of (3-amino-5-chloro-pyridin-2-yl)-(2-chloro-phenyl)-methanone (26.8 mg. 0.10 mmol) and 3.4-dichloro-benzenesulfonyl chloride (24.5 mg, 0.10 mmol) in anhydrous pyridine (1 mL) were stirred overnight at 60° C. Reaction mixture was concentrated and the residue was treated with 1 M NaOH (5 mL) and THF(5 mL) to hydrolyze bis-sulfonamide. The resultant solution was neutralized to pH 6 and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The was purified by preparative HPLC (20→90% gradient of MeCN-water) and pure product fractions were lyophilized to provide 3,4-dichloro-N[5-chloro-2-(2-chloro-benzoyl)-pyridin-3-yl]-benzenesulfonamide as a solid. MS m/z: 498.0 (M+Na).

Aufarbeitung

customReaction mixture
concentrationwas concentrated
additionthe residue was treated with 1 M NaOH (5 mL) and THF(5 mL)
extractionthe aqueous layer was extracted with EtOAc
washThe combined organic extracts were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe was purified by preparative HPLC (20→90% gradient of MeCN-water) and pure product fractions

Quellen und Nachweise

ORD-Eintrag: ord-46c92657e7af450486f0ce4d607e7077
Quelldatensatz: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07622583B2

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