Cyclohexyl-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetic acid → HCID 178523778, compound

HRID 1161310Notes

Reaction equation

HRID 1161310 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.C([O:71][C:72]([C@H:74]1[CH2:79][CH2:78][C@H:77]([NH2:80])[CH2:76][CH2:75]1)=[O:73])C>>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[N:43]([CH:44]([CH:48]3[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]3)[C:45]([NH:80][C@H:77]3[CH2:76][CH2:75][C@H:74]([C:72]([OH:71])=[O:73])[CH2:79][CH2:78]3)=[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

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 178472434HCID 178472434, compoundHCID 178479278HCID 178479278, compound

Product 1

HCID 178523778HCID 178523778, compound

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-cyclohexanecarboxylic acid ethyl ester ([CAS RN 1678-68-8]), followed by subsequent ester hydrolysis in analogy to example 10. Purification was conducted with chiral preparative HPLC (Chiralpak-AD column) eluting with a gradient of ethanol (+0.5% formic acid)/heptane. MS (ES+): 530 (M+H).

Workup

  1. customPurification
  2. washeluting with a gradient of ethanol (+0.5% formic acid)/heptane

Sources & evidence

ORD record
ord-0b58e2706e6c44618037ed6cf6bcbaba
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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