2-[(e)-2-Amino-1-eth-(e)-ylidene-but-2-enylsulfanyl]-5-fluoro-benzoic acid methyl ester → 2-Fluorodibenzo[B,F][1,4]thiazepin-11(10H)-one
Reaction equation
[NH2:1]/[C:2](=[CH:17]/[CH3:18])/[C:3](/[S:6][C:7]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:8]=1[C:9]([OH:11])=O)=[CH:4]\[CH3:5].COC(=O)C1C=C(F)C=CC=1S/C(=C/C)/C(/N)=C\C>>[F:16][C:13]1[CH:14]=[CH:15][C:7]2[S:6][C:3]3[CH:4]=[CH:5][CH:18]=[CH:17][C:2]=3[NH:1][C:9](=[O:11])[C:8]=2[CH:12]=1Participants
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-019b7e8dfc9c4dcc8e02e8f144fe4500
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653257B2
Reaction notes
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