Cyclohexyl-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetic acid → (4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-cyclohexyl)-acetic acid ethyl ester

HRID 1161311Notes

Reaction equation

HRID 1161311 reaction equation
C1(C(N2C3C=C(F)C(F)=CC=3N=C2C2C(OC)=NC(OC)=CC=2)C(O)=O)CCCCC1.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[N:43]([CH:44]([CH:48]3[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]3)[C:45](O)=[O:46])[C:42]3[CH:54]=[C:55]([F:59])[C:56]([F:58])=[CH:57][C:41]=3[N:40]=2)=[CH:35][CH:34]=1.Cl.N[C@H]1CC[C@H](O)CC1.Cl.[CH2:70]([O:72][C:73](=[O:82])[CH2:74][C@H:75]1[CH2:80][CH2:79][C@H:78]([NH2:81])[CH2:77][CH2:76]1)[CH3:71]>>[CH2:70]([O:72][C:73](=[O:82])[CH2:74][CH:75]1[CH2:76][CH2:77][CH:78]([NH:81][C:45](=[O:46])[CH:44]([N:43]2[C:42]3[CH:54]=[C:55]([F:59])[C:56]([F:58])=[CH:57][C:41]=3[N:40]=[C:39]2[C:36]2[CH:35]=[CH:34][C:33]([Cl:32])=[CH:38][CH:37]=2)[CH:48]2[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]2)[CH2:79][CH2:80]1)[CH3:71]

Participants

5

Reactant 4

HCID 66619285Cyclohexyl-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetic acidHCID 66619321[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid2×HCID 178471807HCID 178471807, compoundHCID 178479278HCID 178479278, compound

Product 1

HCID 68645327(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-cyclohexyl)-acetic acid ethyl ester

Procedure

The title compound was prepared in analogy to example 8 replacing cyclohexyl-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetic acid with [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid (example 22, intermediate c) and trans-4-amino-cyclohexanol hydrochloride with trans-(4-amino-cyclohexyl)-acetic acid ethyl ester hydrochloride ([CAS RN 76308-26-4]). MS (ES+): 572 (M+H).

Sources & evidence

ORD record
ord-5db389771e724659a815028d1c31dabb
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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