N-methyl-2-pyrrolidone → HCID 58597372, compound

HRID 1444047Notes

Reaction equation

HRID 1444047 reaction equation
Br[C:2]1[C:3]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[Cl:20])(=[O:12])=[O:11])=[N:4][CH:5]=[C:6](Br)[N:7]=1.C[C:22](C)([O-:24])C.[K+].C[N:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33]>O1CCCC1.C(O)(=O)C.O>[Cl:20][C:14]1[C:15]([Cl:19])=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([NH:9][C:3]1[C:2]([O:24][CH2:22][C:32]2[N:28]=[C:29]([CH3:30])[O:33][CH:31]=2)=[N:7][CH:6]=[CH:5][N:4]=1)(=[O:12])=[O:11]

Participants

7

Reactant 3

HCID 13387N-methyl-2-pyrrolidone2×HCID 23665647Potassium tert-butoxideHCID 591682192,3-Dichloro-N-(3,5-dibromo-2-pyrazinyl)benzenesulphonamide

Product 1

HCID 58597372HCID 58597372, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Examples 146-165 were prepared using the following procedure To a solution of N-(3,5-dibromo-2-pyrazinyl)-2,3-dichlorobenzenesulphonamide (Example 31) (0.003 g) and primary alcohol (0.026 mL of a 0.5M solution in N-methylpyrrolidinone) in N-methylpyrrolidinone (0.1 mL) was added potassium tert-butoxide (0.050 mL of a 1M solution in tetrahydrofuran). The solution was allowed to stand for 24 hours. The reaction mixture was diluted with acetic acid (0.010 mL) and water (0.10 mL) and the solvents were evaporated. The residue was redissolved in dimethylsulphoxide (0.5 mL) and purified by mass directed high pressure liquid chromatography. The solvent was evaporated to afford a solid.

Workup

  1. customExamples 146-165 were prepared
  2. customthe solvents were evaporated
  3. dissolutionThe residue was redissolved in dimethylsulphoxide (0.5 mL)
  4. custompurified by mass
  5. customThe solvent was evaporated
  6. customto afford a solid

Sources & evidence

ORD record
ord-89af2188f70b4f9bbf97da08e04b9c44
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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