Lithium Hydroxide → [8-Chloro-4-difluoromethoxy-2-ethyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid

HRID 1944298Notes

Reaction equation

HRID 1944298 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:31][CH:32]([F:34])[F:33])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1.Cl>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:35])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH2:17][CH3:18])[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)=[CH:24][CH:25]=1)=[C:8]2[O:31][CH:32]([F:33])[F:34]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67459216[8-Chloro-4-difluoromethoxy-2-ethyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester

Product 1

HCID 25095817[8-Chloro-4-difluoromethoxy-2-ethyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acidYield 64.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [8-chloro-4-difluoromethoxy-2-ethyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.56 g) in tetrahydrofuran (20 mL) was treated with 1.0M aqueous lithium hydroxide solution (2.4 mL), and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was diluted with 0.1M aqueous hydrochloric acid solution, concentrated under reduced pressure and then extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by trituration with a mixture of methanol and water, followed by column chromatography on C-18 column to afford title compound (0.35 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by trituration with a mixture of methanol and water

Sources & evidence

ORD record
ord-ac4a90e3299d4c32b59d8814f323ab4e
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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