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

HRID 417116Notes

Reaction equation

HRID 417116 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]([CH3:49])[C:46]([OH:50])=[C:45]([CH3:51])[CH:44]=1>>[CH3:40][O:41][C:42](=[O:52])[C:43]1[CH:48]=[C:47]([CH3:49])[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:45]([CH3:51])[CH:44]=1

Participants

3

Reactant 2

HCID 12389264Methyl 4-hydroxy-3,5-dimethylbenzoateHCID 461857196-{2-Cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethoxy}-nicotinic acid2×

Product 1

HCID 666192674-{2-Cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethoxy}-3,5-dimethyl-benzoic acid methyl esterYield 27%

Procedure

The title compound was prepared according 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), 4-hydroxy-3,5-dimethyl-benzoic acid methyl ester (commercially available), tri-N-butylposphine and N′N′N′N-tetramethylazodicarboxamide. The resulting powder 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) to give the desired compound as an off-white solid (27%). MS (Turbo Spray): m/z=580.3 [M+H].

Workup

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

Sources & evidence

ORD record
ord-07f807b32d0540d989221b21bb644be5
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

Loading…