Sodium Hydroxide → 1-[({4-methyl-6'-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3'-bipyridin-6-yl}oxy)methyl]-cyclobutanecarboxylic acid

HRID 623910Notes

Reaction equation

HRID 623910 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12][CH2:11]2)[N:5]=[CH:4][C:3]=1[C:19]1[CH:20]=[N:21][C:22]([C:25]2[N:26]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[N:29]=2)=[CH:23][CH:24]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11]2)[N:5]=[CH:4][C:3]=1[C:19]1[CH:20]=[N:21][C:22]([C:25]2[N:26]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:39])([CH3:41])[CH3:40])[CH:27]=[C:28]([C:30]([F:32])([F:33])[F:31])[N:29]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67975466ethyl 1-[({4-methyl-6'-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3'-bipyridin-6-yl}oxy)methyl]-cyclobutanecarboxylate

Product 1

HCID 679753041-[({4-methyl-6'-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3'-bipyridin-6-yl}oxy)methyl]-cyclobutanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (7 mL) was added to ethyl 1-[({4-methyl-6′-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3′-bipyridin-6-yl}oxy)methyl]-cyclobutanecarboxylate (343 mg), 1N aqueous sodium hydroxide solution (2.9 mL) was further added to the mixture and the resulting mixture was refluxed for 1 hour. Methanol was distilled off under reduced pressure, and the residue was neutralized by 1N hydrochloric acid. The mixture was extracted with ethyl acetate, the organic layer was washed with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 1-[({4-methyl-6′-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3′-bipyridin-6-yl}oxy)methyl]-cyclobutanecarboxylic acid.

Workup

  1. additionwas further added to the mixture
  2. temperaturethe resulting mixture was refluxed for 1 hour
  3. distillationMethanol was distilled off under reduced pressure
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with a saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3f6b5925439441c9a7a2e9195723191
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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