1,1-Bis(methylthio)-2-nitroethylene → HCID 67051949, Verbindung

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Reaktionsgleichung

[NH2:1][CH2:2][C:3]1([OH:26])[CH2:6][N:5]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([F:16])[C:10]=2[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])=[O:8])[CH2:4]1.[CH3:27][S:28][C:29](SC)=[CH:30][N+:31]([O-:33])=[O:32]>C(O)C>[F:16][C:11]1[C:10]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])=[C:9]([C:7]([N:5]2[CH2:6][C:3]([CH2:2][NH:1]/[C:29](/[S:28][CH3:27])=[CH:30]/[N+:31]([O-:33])=[O:32])([OH:26])[CH2:4]2)=[O:8])[CH:14]=[CH:13][C:12]=1[F:15]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A solution of 3-(aminomethyl)-1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)azetidin-3-ol (0.24 g, 0.5 mmol), prepared using procedures similar to those described in Example 3, and commercially available 1,1-bis(methylthio)-2-nitroethylene (0.083 g, 0.5 mmol) in ethanol (5 mL) was stirred at 70° C. for 16 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to afford 0.10 g, (39%) 1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-({[(Z)-1-(methylthio)-2-nitroethenyl]amino}methyl)azetidin-3-ol. MS (EI) for C20H18F3IN4O4S: 595 (MH+).

Aufarbeitung

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-9a813bd7ad294862aca6fc308c180d10
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07915250B2

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