Bromoacetic Acid → 2-bromo-N-(3-(N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)acetamide

HRID 1669949

Reaction equation

HRID 1669949 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=O.CC(N=C=NC(C)C)C.[NH2:15][C:16]1[CH:17]=[C:18]([S:22]([NH:25][C:26]2[C:35]([NH:36][C:37]3[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[C:39]([O:45][CH3:46])[CH:38]=3)=[N:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1>C(Cl)Cl>[Br:1][CH2:2][C:3]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22](=[O:23])(=[O:24])[NH:25][C:26]2[C:35]([NH:36][C:37]3[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[C:39]([O:45][CH3:46])[CH:38]=3)=[N:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH:17]=1)=[O:5]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 12734DiisopropylcarbodiimideHCID 574484483-amino-N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)benzenesulfonamide

Product 1

HCID 592491652-bromo-N-(3-(N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottom flask was added 2-bromoacetic acid (1.87 g, 13.5 mmol), N,N-diisopropylcarbodiimide (860 mg, 6.8 mmol) and 10 mL DCM. To this mixture was added 3-amino-N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)benzenesulfonamide (2.03 g, 4.5 mmol), prepared using procedures similar to those in Example 168. The reaction was stirred overnight at room temperature. Complete consumption of the starting aniline was confirmed by LCMS. The solvent was evaporated off to yield the crude product (2-bromo-N-(3-(N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)acetamide). This was used directly in the next step without further purification.

Workup

  1. customprepared
  2. customconsumption of the starting aniline
  3. customThe solvent was evaporated off
  4. customto yield the crude product (2-bromo-N-(3-(N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)sulfamoyl)phenyl)acetamide)
  5. customThis was used directly in the next step without further purification

Sources & evidence

ORD record
ord-47ab708e51004c9a982c8b2abb75130a
Source dataset
uspto-grants-2011_08
Patent number
US07989622B2

Linked notes

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