Hydrochloric Acid → 3-isobutyl-7-(5-methyl-pyridin-2-yl)-3H-benzoimidazole-5-carboxylic acid

HRID 59816Notes

Reaction equation

HRID 59816 reaction equation
C[O:2][C:3]([C:5]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)[C:8]2[N:9]=[CH:10][N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-].Cl>CO.O>[CH2:12]([N:11]1[C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=3)[C:8]=2[N:9]=[CH:10]1)[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 596277643-Isobutyl-7-(5-methyl-pyridin-2-yl)-3H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 596277743-isobutyl-7-(5-methyl-pyridin-2-yl)-3H-benzoimidazole-5-carboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-isobutyl-7-(5-methyl-pyridin-2-yl)-3H-benzoimidazole-5-carboxylic acid methyl ester 207 mg, 0.64 mmol) was suspended in a mixture of methanol (10 mL) and water (2 mL). To this suspension was added LiOH (46 mg, 1.92 mmol). The mixture was stirred overnight at room temperature, then made acidic by addition of 1N aqueous HCl, and concentrated to dryness under reduced pressure. The residue was re-dissolved in methanol, filtered to remove insolubles, and the filtrate was concentrated under reduced pressure to provide 165 mg (84%) of 3-isobutyl-7-(5-methyl-pyridin-2-yl)-3H-benzoimidazole-5-carboxylic acid.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. dissolutionThe residue was re-dissolved in methanol
  3. filtrationfiltered
  4. customto remove insolubles
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-43ccf370a5934f37a798a32656d30d54
Source dataset
uspto-grants-2016_09
Patent number
US09440956B2

Reaction notes

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