Water → HCID 70664673, compound

HRID 1403639Notes

Reaction equation

HRID 1403639 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:10]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[N:11][C:12]3[C:17]([N:18]=2)=[CH:16][C:15]([C:19]([O:21]C)=[O:20])=[CH:14][CH:13]=3)[C@@H:5]([CH3:30])[CH2:4]1)[CH3:2].[OH-].[Na+].O>CO>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:10]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)=[N:11][C:12]3[C:17]([N:18]=2)=[CH:16][C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=3)[C@@H:5]([CH3:30])[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70654261HCID 70654261, compound

Product 1

HCID 70664673HCID 70664673, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 3-(4-ethyl-2-methylpiperazin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (80 mg, crude) in methanol (30 mL) was added sodium hydroxide (31.0 mg, 0.78 mmol) and water (1 mL), and the reaction was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, dissolved in water (30 mL), and adjusted to pH 5 with HCl (3N) to give the precipitate, which was purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, water with 0.05% NH3.H2O and CH3CN (10% CH3CN up to 45% in 10 min); Detector, UV 220 nm] to afford (S)-3-(4-ethyl-2-methylpiperazin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid (40 mg, 52.0%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water (30 mL)
  3. customto give the precipitate, which
  4. customwas purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC)
  5. waitmobile phase, water with 0.05% NH3.H2O and CH3CN (10% CH3CN up to 45% in 10 min)

Sources & evidence

ORD record
ord-56a245d4412446aa8fc47c88420cfb86
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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