[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-3-cyano-5-fluoro-benzoic acid methyl ester

HRID 1161346Notes

Reaction equation

HRID 1161346 reaction equation
C(OC(=O)C1C=CC(NC(=O)C(N2C3C=C(F)C(F)=CC=3N=C2C2C=CC(Cl)=CC=2)C2CCCCC2)=CC=1)C.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[N:51]([CH:52]([CH:56]3[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]3)[C:53](O)=[O:54])[C:50]3[CH:62]=[C:63]([F:67])[C:64]([F:66])=[CH:65][C:49]=3[N:48]=2)=[CH:43][CH:42]=1.[CH3:68][O:69][C:70](=[O:81])[C:71]1[CH:76]=[C:75]([F:77])[C:74]([NH2:78])=[C:73]([C:79]#[N:80])[CH:72]=1>>[CH3:68][O:69][C:70](=[O:81])[C:71]1[CH:76]=[C:75]([F:77])[C:74]([NH:78][C:53](=[O:54])[CH:52]([N:51]2[C:50]3[CH:62]=[C:63]([F:67])[C:64]([F:66])=[CH:65][C:49]=3[N:48]=[C:47]2[C:44]2[CH:45]=[CH:46][C:41]([Cl:40])=[CH:42][CH:43]=2)[CH:56]2[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61]2)=[C:73]([C:79]#[N:80])[CH:72]=1

Participants

4

Reactant 3

HCID 66619321[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acidHCID 686454934-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-benzoic acid ethyl esterHCID 686489214-Amino-3-cyano-5-fluoro-benzoic acid methyl ester

Product 1

HCID 686462284-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-3-cyano-5-fluoro-benzoic acid methyl ester

Procedure

The title compound was prepared in analogy to example 22, intermediate d), from [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid and 4-amino-3-cyano-5-fluoro-benzoic acid methyl ester (Arzneimittel Forschung, 34(II), Nr. 11a, 1984; 1612-1624) to give the product as a light brown solid (20%).

Sources & evidence

ORD record
ord-48168795362648bf9cc2c528277df2eb
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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