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

HRID 1809000Notes

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-a7d0f8f8281b4b1a83af090b3db03af3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362002B2

Reaction notes

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