HCID 67458282, compound → HCID 25097595, compound

HRID 1922155Notes

Reaction equation

HRID 1922155 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([CH3:32])=[C:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[CH:30][CH:29]=[N:28]3)=[CH:23][CH:22]=1)[C:10]([CH:17]([CH3:19])[CH3:18])=[N:11]2>O1CCCC1.[OH-].[Li+]>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH:17]([CH3:18])[CH3:19])[C:9]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[CH:30][CH:29]=[N:28]3)=[CH:23][CH:22]=1)=[C:8]2[CH3:32]

Participants

4

Reactant 1

HCID 67458282HCID 67458282, compound

Product 1

HCID 25097595HCID 25097595, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [8-chloro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.087 g) in tetrahydrofuran (3.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.5 mL) was stirred at room temperature for three hours. The mixture was concentrated under reduced pressure and the pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid (3 mL). The mixture was extracted with ethyl acetate and the combined extracts washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of cyclohexane, ethyl acetate and formic acid (1:0:0:0.001 to 0:1:0.001 by volume) to afford title compound as pale yellow solid (0.06 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid (3 mL)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined extracts washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography on silica gel
  8. washeluting with a mixture of cyclohexane, ethyl acetate and formic acid (1:0:0:0.001 to 0:1:0.001 by volume)

Sources & evidence

ORD record
ord-8fa893734a0c4352b19da81566ebed97
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

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