Hydrochloric Acid → 4-{[(3,5-Dichlorophenyl)(1-methyl-1h-benzimidazol-2-yl)amino]methyl}-benzoic acid

HRID 230011Notes

Reaction equation

HRID 230011 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=2)[C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Li+].[OH-].CCOC(C)=O.Cl>O1CCOCC1.O>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]([CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)[C:10]2[N:14]([CH3:15])[C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 68835443Methyl 4-{[(3,5-dichlorophenyl)(1-methyl-1H-benzimidazol-2-yl)amino]-methyl}benzoate

Product 1

HCID 688361824-{[(3,5-Dichlorophenyl)(1-methyl-1h-benzimidazol-2-yl)amino]methyl}-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To the title compound of Example 223 Step B (0.2 mmol, 85 mg) in 1.6 mL of dioxane was added a solution of LiOH (0.8 mmol, 19 mg) in 0.8 mL of H2O. The reaction was allowed to stir at ambient temperature overnight. The crude reaction mixture was poured into pH 7 buffer/EtOAc, which was acidified with 2 N HCl until two clear layers formed after agitation. The organic phase was collected and the aqueous phase was extracted twice with EtOAc. The combined organic phase was dried over MgSO4, then concentrated under reduced pressure to afford the product as a white foam. MS (ESI): m/z 426 (M+H). HPLC A: 1.79 min.

Workup

  1. customThe crude reaction mixture
  2. customformed after agitation
  3. customThe organic phase was collected
  4. extractionthe aqueous phase was extracted twice with EtOAc
  5. dry with materialThe combined organic phase was dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d002fb82ceac4f72bb3c6dde98500af8
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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