Sodium Hydroxide → 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-(7-methoxyquinolin-3-yl)-1H-pyrazol-1-yl]ethyl}benzoic acid

HRID 1865427Notes

Reaction equation

HRID 1865427 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[N:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[C:19]([O:24][CH3:25])[CH:18]=4)[N:11]([C@H:26]([C:28]3[CH:38]=[CH:37][C:31]([C:32]([O:34]CC)=[O:33])=[CH:30][CH:29]=3)[CH3:27])[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[N:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[C:19]([O:24][CH3:25])[CH:18]=4)[N:11]([C@H:26]([C:28]3[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:37][CH:38]=3)[CH3:27])[N:10]=2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68567756Ethyl 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-(7-methoxyquinolin-3-yl)-1H-pyrazol-1-yl]ethyl}benzoate

Product 1

HCID 685681784-{(1S)-1-[3-(3,5-dichlorophenyl)-5-(7-methoxyquinolin-3-yl)-1H-pyrazol-1-yl]ethyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the intermediate from step G (67 mg, 0.12 mmol) in 4 mL of 1:1 THF/MeOH was added sodium hydroxide (5N, 1 mL). After stirring the reaction at room temperature for 1 hour it was concentrated in vacuo to remove THF/MeOH. The resulting aqueous mixture was acidified with 1N HCl until the pH was slightly acidic (pH=5). The resulting solution was extracted with EtOAc (3×), and the combined organic layers were then washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting white solid was used without further purification.

Workup

  1. customthe reaction at room temperature for 1 hour it
  2. concentrationwas concentrated in vacuo
  3. customto remove THF/MeOH
  4. extractionThe resulting solution was extracted with EtOAc (3×)
  5. washthe combined organic layers were then washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting white solid was used without further purification

Sources & evidence

ORD record
ord-876a640a77d84311a4a1547abb02d276
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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