Benzenesulfonamide → N-(3-chloropyrido[2,3-b]pyrazin-2-yl)benzenesulfonamide

HRID 655624Notes

Reaction equation

HRID 655624 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[N:9][C:5]2=[N:6][C:7]=1[Cl:8].[C:13]1([S:19]([NH2:22])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:8][C:7]1[N:6]=[C:5]2[N:9]=[CH:10][CH:11]=[CH:12][C:4]2=[N:3][C:2]=1[NH:22][S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 117888682,3-Dichloropyrido[2,3-b]pyrazine

Product 1

HCID 57625374N-(3-chloropyrido[2,3-b]pyrazin-2-yl)benzenesulfonamideYield 17.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2,3-dichloro-pyrido(2,3-b)pyrazine (300 mg; 1.5 mmol; 1 eq.), benzenesulfonamide (235.8 mg, 1.5 mmol, 1 eq.) and K2CO3 (207.3 mg, 1.5 mmol, 1 eq.) are taken up in anhydrous DMA (10 ml) under argon. The reaction mixture is stirred at room temperature for 7 days. The solvent is evaporated and the residue obtained is purified by prep HPLC using a gradient of H2O, TFA 0.1%/ACN, TFA 0.1%, to afford 82.1 mg (17%) of the title compound. 1H NMR (DMSO-d6) δ 8.67 (dd, J=5.7, 1.5 Hz, 1H), 8.57 (dd, J=7.9, 1.5 Hz, 1H), 8.08 (dd, J=8.0 Hz, 1.8 Hz, 2H), 7.57 (dd, J=7.9, 5.7 Hz, 1H), 7.54-7.46 (m, 4H). HPLC (max plot) 94%; Rt 1.96 min. LC/MS: (ES+): 321.0, (ES−): 319.0.

Workup

  1. customThe solvent is evaporated
  2. customthe residue obtained
  3. customis purified by prep HPLC

Sources & evidence

ORD record
ord-9a200307489b4a969ebcff4e727e645b
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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