6-{2-Cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethoxy}-nicotinic acid → 4-{2-Cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethoxy}-3,5-difluoro-benzoic acid methyl ester

HRID 417126Notes

Reaction equation

HRID 417126 reaction equation
[CH:1]1([CH:7]([N:19]2[C:23]3[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:22]=3[N:21]=[C:20]2[C:30]2[C:31]([O:38][CH3:39])=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[CH2:8]OC2C=CC(C(O)=O)=CN=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:40][O:41][C:42](=[O:52])[C:43]1[CH:48]=[C:47]([F:49])[C:46]([OH:50])=[C:45]([F:51])[CH:44]=1>>[CH3:40][O:41][C:42](=[O:52])[C:43]1[CH:44]=[C:45]([F:51])[C:46]([O:50][CH2:8][CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:19]2[C:23]3[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:22]=3[N:21]=[C:20]2[C:30]2[C:31]([O:38][CH3:39])=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)=[C:47]([F:49])[CH:48]=1

Participants

3

Reactant 2

HCID 461857196-{2-Cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethoxy}-nicotinic acid2×HCID 53847253Methyl 3,5-difluoro-4-hydroxybenzoate

Product 1

HCID 666193384-{2-Cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethoxy}-3,5-difluoro-benzoic acid methyl ester

Procedure

The title compound was prepared in analogy to Example 4, intermediate, from 2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethanol (Example 73, intermediate b), 3,5-difluoro-4-hydroxy-benzoic acid methyl ester (commercially available), tri-N-butylposphine and N′N′N′N-tetramethylazodicarboxylate. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:tert-butyl methyl ether (100:0 to 50:50). Off-white foam (45%). MS (Turbo Spray): m/z=588.3 [M+H].

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:tert-butyl methyl ether (100:0 to 50:50)

Sources & evidence

ORD record
ord-5f6acc4c3c7c479ca7b0d015cc0da66a
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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