Hydrochloric Acid → {3,5-Dichloro-4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid

HRID 1514996Notes

Reaction equation

HRID 1514996 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22](=[O:32])[NH:23][C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([Cl:33])[CH:7]=1.[OH-].[Na+].Cl>CO>[Cl:33][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([Cl:12])[C:9]=1[C:13]1[NH:17][C:16]2[CH:18]=[C:19]([C:22](=[O:32])[NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=3)[CH:20]=[CH:21][C:15]=2[N:14]=1)[O:5][CH2:4][C:3]([OH:34])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66965080{3,5-dichloro-4-[6-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester

Product 1

HCID 66965280{3,5-Dichloro-4-[6-(3,4-dimethyl-phenylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {3,5-dichloro-4-[6-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester (85 mg, 0.17 mmol) in MeOH (3 mL) was added 1N NaOH (3 mL) and the solution was stirred at ambient temperature for 3 h. The solution was carefully acidified to pH 3-4 with 1N HCl and the resulting suspension was filtered, washed with water, was dried under reduced pressure to give the title compound. 1H NMR (Methanol-d4, 400 MHz): δ 8.29 (d, 1H), 7.96 (dd, 1H), 7.76 (dd, 1H), 7.49 (d, 1H), 7.45 (dd, 1H), 7.23 (s, 2H), 7.15 (d, 1H), 4.84 (s, 2H), 2.30 (s, 3H), 2.27 (s, 3H). MS (m/z) 484.1 (M+1); retention time: 1.18 min (Method 10).

Workup

  1. filtrationthe resulting suspension was filtered
  2. washwashed with water
  3. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-8d1cf67e29b94f00bff649dad8822629
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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