Lithium Hydroxide → HCID 25097870, compound

HRID 1944373Notes

Reaction equation

HRID 1944373 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]2[C:6]=1[C:7]([CH3:31])=[C:8]([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:9]([CH:16]([CH3:18])[CH3:17])=[N:10]2.[OH-].[Li+]>O1CCCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:5]([CH2:4][C:3]([OH:32])=[O:2])=[C:6]2[C:11]=1[N:10]=[C:9]([CH:16]([CH3:17])[CH3:18])[C:8]([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:7]2[CH3:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67457614HCID 67457614, compound

Product 1

HCID 25097870HCID 25097870, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [8-chloro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yl]acetic acid methyl ester (0.04 g) in tetrahydrofuran (3.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.3 mL), and the resulting mixture was stirred at room temperature for six hours. The mixture was concentrated under reduced pressure and the pH adjusted to 4 by the addition of 0.1M aqueous hydrochloric acid (3.0 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 preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (5:95 to 98:2 by volume) to afford title compound as white solid (0.024 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe pH adjusted to 4 by the addition of 0.1M aqueous hydrochloric acid (3.0 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 preparative reverse-phase HPLC
  8. washeluting with a mixture of acetonitrile and water (5:95 to 98:2 by volume)

Sources & evidence

ORD record
ord-ebd179bba82b4e1b886135ea41d4db2c
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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