Hydrochloric Acid → HCID 70654239, compound

HRID 1405326Notes

Reaction equation

HRID 1405326 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N:27](S(C)(=O)=O)[S:28]([CH3:31])(=[O:30])=[O:29])[CH:15]=3)[N:10]=2)=[CH:5][CH:4]=1.O[Li].O.[OH-].[Na+].Cl>O1CCCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:15]=3)[N:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 70654333HCID 70654333, compound

Product 1

HCID 70654239HCID 70654239, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of N-(2,3-bis(4-methoxyphenyl)quinoxalin-6-yl)-N-(methylsulfonyl)methanesulfonamide (143.64 mg, 0.28 mmol, 1.00 equiv, 90%) in tetrahydrofuran/MeOH (1:1, 10 mL) was added LiOH H2O (58.5 mg, 1.39 mmol, 5.00 equiv). This was followed by the dropwise addition of a solution of sodium hydroxide (56 mg, 1.40 mmol, 5.00 equiv) in water (2 mL). The resulting solution was stirred for 1 h at 35° C. in an oil bath. The pH was adjusted to 7-8 with 1N HCl. The resulting mixture was concentrated in vacuo and washed with methanol, resulting in 46.5 mg (37%) of N-(2,3-bis(4-methoxyphenyl)quinoxalin-6-yl)methanesulfonamide as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. washwashed with methanol
  3. customresulting in 46.5 mg (37%) of N-(2,3-bis(4-methoxyphenyl)quinoxalin-6-yl)methanesulfonamide as a yellow solid

Sources & evidence

ORD record
ord-876b07108da943c9b82c2a790f19f032
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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