Sodium Hydroxide → HCID 178426559, compound

HRID 1514982Notes

Reaction equation

HRID 1514982 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([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:21][C:15]=3[N:14]=2)=[C:8]([CH3:33])[CH:7]=1.[OH-].[Na+]>CO>[CH3:31][C:26]1[CH:25]=[C:24]([NH:23][C:22]([C:20]2[CH:19]=[CH:18][C:16]3[NH:17][C:13]([C:9]4[C:8]([CH3:33])=[CH:7][C:6]([NH:5][CH2:4][C:3]([OH:34])=[O:2])=[CH:11][C:10]=4[CH3:12])=[N:14][C:15]=3[CH:21]=2)=[O:32])[CH:29]=[CH:28][C:27]=1[CH3:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501558HCID 178501558, compound

Product 1

HCID 178426559HCID 178426559, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of {4-[5-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethyl-phenylamino}-acetic acid methyl ester (160 mg) in MeOH (5 mL) was added 1N NaOH (5 mL) and the mixture was stirred at room temperature for 18 h. The solution was washed with Et2O and the aqueous layer was carefully acidified to pH=2-3 with 1N HCl. The resulting suspension was filtered, washed with water and dried to give {4-[5-(3,4-dimethylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenylamino}-acetic acid as a white solid. MS (ESI)m/z 443 (M+H). 1H NMR (MeOD, 400 MHz) δ 8.22 (s, 1H), 7.91 (dd, 1H), 7.70 (d, 1H), 7.46 (d, 1H), 7.42 (dd, 1H), 7.12 (d, 1H), 6.44 (s, 2H), 3.91 (s, 2H), 2.29 (s, 3H), 2.26 (s, 3H), 2.10 (s, 6H).

Workup

  1. washThe solution was washed with Et2O
  2. filtrationThe resulting suspension was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-31835302f3044bb998cd5c9e24f78293
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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