Water → HCID 50991568, compound

HRID 1403552Notes

Reaction equation

HRID 1403552 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:35])[C:15]2[C:16]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[N:17][C:18]3[C:23]([N:24]=2)=[CH:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][CH:19]=3)[CH2:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+].O>CO>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:16]2[C:15]([N:14]([CH3:35])[CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:25]([OH:27])=[O:26])[CH:22]=3)[N:17]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70664710HCID 70664710, compound

Product 1

HCID 50991568HCID 50991568, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-((1-(tert-butoxycarbonyl)piperidin-4-yl)(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid (90.0 mg, 0.23 mmol) in MeOH (20 mL) was added sodium hydroxide (50 mg, 1.25 mol) and 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 to pH 6 with hydrochloric acid (1N) and concentrated in vacuo. The crude product was purified by Prep-HPLC with the following conditions (3#-Agilent 1200 prep HPLC): Column, X-Bridge Prep C18,19*150 mm; mobile phase, water with 0.5% TFA:CH3CN=(25%-37% CH3CN in 9.0 min); Detector, 5 μm to afford 2-(4-fluorophenyl)-3-(methyl(piperidin-4-yl)amino)quinoxaline-6-carboxylic acid as a yellow solid (22 mg, 25%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (5 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by Prep-HPLC with the following conditions (3#-Agilent 1200 prep HPLC)
  5. customCH3CN=(25%-37% CH3CN in 9.0 min)

Sources & evidence

ORD record
ord-a2f109e949cd44869612e9ce8531c561
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…