Sodium Hydroxide → HCID 70664989, compound

HRID 1403557Notes

Reaction equation

HRID 1403557 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[C:24]([F:27])([F:26])[F:25])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:28]([O:30]C)=[O:29])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[C:24]([F:27])([F:26])[F:25])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:28]([OH:30])=[O:29])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70664856HCID 70664856, compound

Product 1

HCID 70664989HCID 70664989, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-[(2R)-2-(trifluoromethyl)piperidin-1-yl]quinoxaline-6-carboxylate (15 mg, crude) in methanol (15 mL) was added sodium hydroxide (10 mg, 0.25 mmol) in water (1 mL). The resulting solution was stirred overnight at room temperature and concentrated in vacuo. The residue was dissolved in water (5 mL) and adjusted pH to 6 with HCl (1N), then extracted with dichloromethane (4×10 mL) and the organic layers combined and dried over anhydrous magnesium sulfate and concentrated in vacuo to give a residue. Purification via Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, water with 0.05% NH3 and CH3CN (10% CH3CN up to 45% in 7 min); Detector, UV 220 nm] afforded 2-(4-fluorophenyl)-3-[(2R)-2-(trifluoromethyl)piperidin-1-yl]quinoxaline-6-carboxylic acid as a yellow solid (9 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (5 mL)
  3. extractionextracted with dichloromethane (4×10 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. customPurification via Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC)
  8. waitmobile phase, water with 0.05% NH3 and CH3CN (10% CH3CN up to 45% in 7 min)

Sources & evidence

ORD record
ord-3780ebb888b6408cbc17fd8e60a3cc8f
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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