Hydrochloric Acid → HCID 66965217, compound

HRID 1514997Notes

Reaction equation

HRID 1514997 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15]3[CH:17]=[C:18]([C:21](=[O:31])[NH:22][C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([CH3:30])[CH:24]=4)[CH:19]=[CH:20][C:14]=3[N:13]=2)=[C:8]([Cl:32])[CH:7]=1.[OH-].[Na+].Cl>CO>[Cl:32][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[C:12]1[NH:16][C:15]2[CH:17]=[C:18]([C:21](=[O:31])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([CH3:30])[CH:24]=3)[CH:19]=[CH:20][C:14]=2[N:13]=1)[O:5][CH2:4][C:3]([OH:33])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66965699HCID 66965699, compound

Product 1

HCID 66965217HCID 66965217, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {3-chloro-4-[6-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester (100 mg, 0.21 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 suspension was filtered, washed with water, and the white solid was dried in vacuum oven to give the title compound. 1H NMR (Methanol-d4, 400 MHz): δ 8.26 (s, 1H), 7.92 (dd, 1H), 7.84 (d, 2H), 7.74 (d, 1H), 7.48 (dd, 1H), 7.44 (dd, 1H), 7.23 (dd, 1H), 7.14 (m, 2H), 4.80 (s, 2H), 2.30 (s, 3H), 2.27 (s, 3H). MS (m/z) 450.2 (M+1) Retention time: 1.19 min (Method 10).

Workup

  1. filtrationthe suspension was filtered
  2. washwashed with water
  3. customthe white solid was dried in vacuum oven

Sources & evidence

ORD record
ord-55301f76f8564de98f0faf0d8d6c9b0c
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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