Sodium Hydroxide → 2-Bromo-5-[(4-chloro-phenyl)-5-chloro-2-methyl-phenylamino]-1-isopropyl-1H-imidazole-4-carboxylic acid

HRID 2410096Notes

Reaction equation

HRID 2410096 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:32])[N:11]([CH:29]([CH3:31])[CH3:30])[C:12]=1[N:13]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH3:21])=[O:7])C>C1COCC1.CO>[Br:32][C:10]1[N:11]([CH:29]([CH3:31])[CH3:30])[C:12]([N:13]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[CH3:21])=[C:8]([C:6]([OH:7])=[O:5])[N:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 867077542-bromo-5-[(4-chloro-phenyl)-5-chloro-2-methyl-phenylamino]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

Product 1

HCID 867077532-Bromo-5-[(4-chloro-phenyl)-5-chloro-2-methyl-phenylamino]-1-isopropyl-1H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaOH (100 mL, 2 M aqueous solution, 200 mmol) was added to a solution of 2-bromo-5-[(4-chloro-phenyl)-5-chloro-2-methyl-phenylamino]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester (step E2; 5.0 g, 9.6 mmol) in THF (100 mL) and MeOH (100 mL) at rt and reactants were stirred at rt for 2 h. THF and MeOH were evaporated, then the mixture was diluted in EtOAc/H2O and the pH was adjusted to 5 with diluted HCl. The aqueous layer was extracted once with EtOAc. The organic extract was dried (Na2SO4) and concentrated to afford an off-white foam; ESI-MS: 598.2 [M+H]+ (LC-MS 2); 1H-NMR (DMSO-d6, 400 MHz) δ ppm 1.20 (d, J=18.38 Hz, 3 H) 1.44 (d, J=6.65 Hz, 3 H) 2.16 (s, 3 H) 4.97 (d, J=7.04 Hz, 1 H) 6.62 (dd, J=7.82, 1.95 Hz, 2 H) 6.78 (d, J=2.35 Hz, 1 H) 7.03 (d, J=7.82 Hz, 1 H) 7.27 (m, 2 H) 7.42 (m, J=8.60 Hz, 2 H).

Workup

  1. customTHF and MeOH were evaporated
  2. additionthe mixture was diluted in EtOAc/H2O
  3. extractionThe aqueous layer was extracted once with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated
  7. customto afford an off-white foam

Sources & evidence

ORD record
ord-4f251547cc5647b397187ff212241e5b
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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