Methanol → 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-quinolin-3-yl-1H-pyrazol-1-yl]ethyl}benzoic acid

HRID 1865420Notes

Reaction equation

HRID 1865420 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]=[CH:19][CH:18]=4)[N:11]([C@H:24]([C:26]3[CH:36]=[CH:35][C:29]([C:30]([O:32]CC)=[O:31])=[CH:28][CH:27]=3)[CH3:25])[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CO.[OH-].[Na+]>C1COCC1>[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]=[CH:19][CH:18]=4)[N:11]([C@H:24]([C:26]3[CH:36]=[CH:35][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=3)[CH3:25])[N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68568297ethyl 4-{(1S)-1-[3-(3,5-dichlorophenyl)-5-quinolin-3-yl-1H-pyrazol-1-yl]ethyl}benzoate

Product 1

HCID 685700994-{(1S)-1-[3-(3,5-dichlorophenyl)-5-quinolin-3-yl-1H-pyrazol-1-yl]ethyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the intermediate from step D (125 mg, 0.24 mmol) in 5 mL of THF was added MeOH (1 mL) followed by sodium hydroxide (5N, 0.5 mL). After stirring the reaction at room temperature for 18 hours, 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. LC-MS: 4.03 min; (M+H)=488.3.

Workup

  1. customthe reaction at room temperature for 18 hours
  2. concentrationit was 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
  10. custom4.03 min

Sources & evidence

ORD record
ord-a5954055300948febc241adb4baba177
Source dataset
uspto-grants-2009_12
Patent number
US07625938B2

Reaction notes

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