2-Aminothiophenol → 2-[(e)-2-Amino-1-eth-(e)-ylidene-but-2-enylsulfanyl]-5-fluoro-benzoic acid methyl ester
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[CH3:9][O:10][C:11](=[O:20])[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1F>>[CH3:9][O:10][C:11](=[O:20])[C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[S:8]/[C:3](=[CH:4]/[CH3:5])/[C:2](/[NH2:1])=[CH:7]\[CH3:6]Participants
3
Procedure
Thus, 2-aminobenzenethiol may be reacted with 2,5-difluoro-benzoic acid methyl ester to form a 2-[(E)-2-amino-1-eth-(E)-ylidene-but-2-enylsulfanyl]-5-fluoro-benzoic acid methyl ester intermediate that can be converted by treatment with alkali to 2-[(E)-2-amino-1-eth-(E)-ylidene-but-2-enylsulfanyl]-5-fluoro-benzoic acid. The benzoic acid can be cyclized to form 2-fluoro-10H-dibenzo[b,f][1,4]thiazepin-11-one, that may be converted to 11-chloro-2-fluoro-dibenzo[b,f][1,4]thiazepine, that may be further reacted with piperazine to form the title compound.
Sources & evidence
- ORD record
- ord-6f4775bb650d4f7eb608eb39637e9439
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653257B2
Reaction notes
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