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

HRID 605740Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 70 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-9a813bd7ad294862aca6fc308c180d10
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915250B2

Reaction notes

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