Water → N-(2-chloropyrido[3,4-b]pyrazin-3-yl)benzenesulfonamide

HRID 655623Notes

Reaction equation

HRID 655623 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1Cl.[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+].O>CC(N(C)C)=O>[Cl:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][N:10]=[CH:9][C:5]2=[N:6][C:7]=1[NH:22][S:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 231227312,3-Dichloropyrido[3,4-b]pyrazine

Product 1

HCID 57625398N-(2-chloropyrido[3,4-b]pyrazin-3-yl)benzenesulfonamideYield 5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2,3-dichloro-pyrido(3,4-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 3 days, then water (15 ml) is added. The aqueous phase is washed with EtOAc (4×10 ml) then lyophilized. The solid residue obtained is extracted with DCM and the solvent is evaporated to near dryness then purified by preparative HPLC using a gradient of H2O, TFA 0.1% ACN, TFA 0.1%, to afford 21.7 mg (5%) of the title compound. 1H NMR (DMSO-d6) δ 9.13 (s, 1H), 8.42 (d, J=6.7 Hz, 1H), 8.03-7.97 (m, 2H), 7.56 (d, J=6.8 Hz, 1H), 7.51-7.45 (m, 3H). HPLC (max plot) 95%; Rt 1.71 min. LC/MS: (ES+): 321.0, (ES−): 319.0.

Workup

  1. washThe aqueous phase is washed with EtOAc (4×10 ml)
  2. customThe solid residue obtained
  3. extractionis extracted with DCM
  4. customthe solvent is evaporated
  5. customthen purified by preparative HPLC

Sources & evidence

ORD record
ord-df357a5322bf466a976411bdffc1d83f
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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