Hydrochloric Acid → 2-(2-{2-[1-(4,6,7-trifluoro-1H-benzoimidazol-2-yl)ethyl]-3-methyl-3H-benzoimidazol-5-ylcarbonylamino}ethoxy)benzoic acid

HRID 412730Notes

Reaction equation

HRID 412730 reaction equation
[F:1][C:2]1[C:10]2[N:9]=[C:8]([CH:11]([C:13]3[N:14]([CH3:39])[C:15]4[CH:21]=[C:20]([C:22]([NH:24][CH2:25][CH2:26][O:27][C:28]5[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=5[C:30]([O:32]CC)=[O:31])=[O:23])[CH:19]=[CH:18][C:16]=4[N:17]=3)[CH3:12])[NH:7][C:6]=2[C:5]([F:40])=[C:4]([F:41])[CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[C:10]2[N:9]=[C:8]([CH:11]([C:13]3[N:14]([CH3:39])[C:15]4[CH:21]=[C:20]([C:22]([NH:24][CH2:25][CH2:26][O:27][C:28]5[CH:38]=[CH:37][CH:36]=[CH:35][C:29]=5[C:30]([OH:32])=[O:31])=[O:23])[CH:19]=[CH:18][C:16]=4[N:17]=3)[CH3:12])[NH:7][C:6]=2[C:5]([F:40])=[C:4]([F:41])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18537795ethyl 2-(2-{2-[1-(4,6,7-trifluoro-1H-benzoimidazol-2-yl)ethyl]-3-methyl-3H-benzoimidazol-5-carbonylamino}ethoxy}benzoate

Product 1

HCID 102089732-(2-{2-[1-(4,6,7-trifluoro-1H-benzoimidazol-2-yl)ethyl]-3-methyl-3H-benzoimidazol-5-ylcarbonylamino}ethoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture comprising ethyl 2-(2-{2-[I-(4,6,7-trifluoro-1H-benzoimidazol-2-yl)ethyl]-3-methyl-3H-benzoimidazol-5-carbonylamino}ethoxy}benzoate (118 mg, 0.21 mmol), methanol (4 ml) and 2N sodium hydroxide (2.1 ml) was stirred at room temperature for 4 hours, neutralized with 2N hydrochloric acid (2.1 ml) and partitioned between ethyl acetate and saturated ammonium chloride. The aqueous layer was separated and extracted with ethyl acetate (X3). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to a white solid. The residue was dissolved in warm ethanol (10 ml) and 4M hydrogen chloride/dioxane solution. The solution was diluted with ethyl ether to give a precipitate. The precipitate was isolated and dried to give 2-(2-{2-[1-(4,6,7-trifluoro-1H-benzoimidazol-2-yl)ethyl]-3-methyl-3H-benzoimidazol-5-ylcarbonylamino}ethoxy)benzoic acid as a white solid; MS (LCMS) C27H22F3N5O4 m/e calc 537.50; found 538.4 (MH+).

Workup

  1. custompartitioned between ethyl acetate and saturated ammonium chloride
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (X3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a white solid
  7. dissolutionThe residue was dissolved in warm ethanol (10 ml)
  8. additionThe solution was diluted with ethyl ether
  9. customto give a precipitate
  10. customThe precipitate was isolated
  11. customdried

Sources & evidence

ORD record
ord-cc2b5457f9be42aaab2fe0161e1fcf91
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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