Hydrochloric Acid → (4-Cyano-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591579Notes

Reaction equation

HRID 591579 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][C:5]1[C:9]2[C:10]([C:24]#[N:25])=[CH:11][C:12]([O:14][CH2:15][C:16]3[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)=[CH:13][C:8]=2[S:7][CH:6]=1.C1COCC1.[OH-].[Na+].Cl>CO>[C:24]([C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:26])=[O:2])=[CH:6][S:7][C:8]=2[CH:13]=[C:12]([O:14][CH2:15][C:16]2[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[CH:11]=1)#[N:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118667069Methyl(4-cyano-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89767794(4-Cyano-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl(4-cyano-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (96 mg), THF (3 mL) and MeOH (3 mL) was added 1N NaOH (1.179 mL) at room temperature. The mixture was stirred at room temperature for 12 h. The mixture was neutralized with 1N HCl at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The crystals were crystallized from EtOAc to give the title compound (80 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crystals were crystallized from EtOAc

Sources & evidence

ORD record
ord-6ec5efabd92b4d42b0154058306f66db
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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