Hydrochloric Acid → HCID 59249031, compound

HRID 446667Notes

Reaction equation

HRID 446667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11]1[C:12]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#N)[CH:26]=2)(=[O:24])=[O:23])=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.O1CCOCC1.[OH-:39].[Na+].Cl.C[OH:43]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11]1[C:12]([NH:21][S:22]([C:25]2[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=2)[C:31]([OH:43])=[O:39])(=[O:24])=[O:23])=[N:13][C:14]2[C:19]([N:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 25102201HCID 25102201, compound

Product 1

HCID 59249031HCID 59249031, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-(3-{[2-chloro-5-(methoxy)-phenyl]amino}quinoxalin-2-yl)-3-cyanobenzenesulfonamide (6.02 g, 12.95 mmol), prepared using procedures similar to those in Example 115 or Example 423, in methanol (20 mL) and 1,4-dioxane (20 mL) was added 6.0 N aqueous sodium hydroxide (40 mL) at room temperature. The solution was stirred at 90° C. for 3.5 h. The reaction was cooled to room temperature and neutralized slowly by adding 2.0 N hydrochloric acid until the pH of the solution became in the 2-3 range at 0° C. The solution was diluted with ethyl acetate (300 mL). The organic layer was washed with saturated aqueous sodium chloride (50 mL) and dried over magnesium sulfate. Filtration and concentration at reduced pressure afforded 3-{[(3-{[2-chloro-5-(methoxy)-phenyl]amino}quinoxalin-2-yl)amino]sulfonyl}benzoic acid (5.921 g, 94%). MS (EI) m/z for C22H17ClN4O5S: 485.0 (MH+).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. custombecame in the 2-3 range at 0° C
  3. washThe organic layer was washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration at reduced pressure

Sources & evidence

ORD record
ord-07b50e1a58444b159ac127c97391a972
Source dataset
uspto-grants-2013_07
Patent number
US08481001B2

Reaction notes

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