Sodium Hydroxide → 1-[({5'-chloro-4-methyl-6'-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]-3,3'-bipyridin-6-yl]oxy)methyl}cyclobutanecarboxylic acid

HRID 623919Notes

Reaction equation

HRID 623919 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:27]2[CH:28]=[N:29][C:30]([O:34][CH2:35][C:36]3([C:40]([O:42]CC)=[O:41])[CH2:39][CH2:38][CH2:37]3)=[CH:31][C:32]=2[CH3:33])[CH:7]=[N:8][C:9]=1[C:10]1[N:11]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1>CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:27]2[CH:28]=[N:29][C:30]([O:34][CH2:35][C:36]3([C:40]([OH:42])=[O:41])[CH2:37][CH2:38][CH2:39]3)=[CH:31][C:32]=2[CH3:33])[CH:7]=[N:8][C:9]=1[C:10]1[N:11]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:24])[CH3:25])[CH:12]=[C:13]([C:15]([F:17])([F:16])[F:18])[N:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86698180ethyl 1-[({5'-chloro-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 679753101-[({5'-chloro-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) and 1N aqueous sodium hydroxide solution (2.6 mL) were added to ethyl 1-[({5′-chloro-4-methyl-6′-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-imidazol-2-yl]-3,3′-bipyridin-6-yl}oxy)methyl]cyclobutanecarboxylate (327 mg), and the 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, and dried over anhydrous magnesium sulfate. The mixture was concentrated under reduced pressure to obtain 1-[({5′-chloro-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. temperaturethe mixture was refluxed for 1 hour
  2. distillationMethanol was distilled off under reduced pressure
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-66836ae47cdc45e7bf79e328b6b4cae1
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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